Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from Boston to Chicago is Frontier Airlines.
Cheapest Month
May
Travel Period: May 2024 - April 2025
The cheapest month(s) to fly from Boston to Chicago is May.
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May 2024
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Jun 2024
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Jul 2024
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Aug 2024
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Sep 2024
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Oct 2024
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Nov 2024
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Dec 2024
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Jan 2025
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Feb 2025
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Mar 2025
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Apr 2025
Cheapest Day of the Week
Wednesday
The cheapest day(s) of the week to fly from Boston to Chicago is Wednesday.
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Sun Sunday
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Mon Monday
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Tue Tuesday
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Wed Wednesday
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Thu Thursday
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Fri Friday
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Sat Saturday
Cheapest Time
8am
The cheapest time of the day to fly from Boston to Chicago is in the morning.
Early Morning 12:01am - 06:00am
Morning 6:01am - 12:00pm
Afternoon 12:01pm - 6:00pm
Evening 6:01pm to 12:00am
12am
6am
12pm
6pm
Flight Schedules
Last Updated: Tue, 2 Apr, 2024
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Total Duration
- Shortest
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All
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Availability
- M
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- S
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20:17 - 22:07BOS - ORD
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20:17 (BOS)Boston Logan International Airport
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22:07 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1464)Boeing 737 800 - 2h 50m
- Direct
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- M
- T
- W
- T
- F
- -
- S
- Boeing 737 800
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20:40 - 22:42BOS - ORD
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20:40 (BOS)Boston Logan International Airport
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22:42 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 2685)Airbus A220 100 Passenger - 3h 02m
- Direct
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- M
- T
- W
- T
- F
- -
- S
- Airbus A220 100 Passenger
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21:55 - 23:30BOS - MDW
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21:55 (BOS)Boston Logan International Airport
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23:30 (MDW)Chicago Midway Airport
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(WN 5774)Boeing 737 800 - 2h 35m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
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05:45 - 07:40BOS - ORD
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05:45 (BOS)Boston Logan International Airport
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07:40 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 2265)Boeing 737 800 - 2h 55m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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06:00 - 08:00BOS - ORD
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06:00 (BOS)Boston Logan International Airport
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08:00 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 567)Boeing 737 900 - 3h
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 900
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06:40 - 08:15BOS - MDW
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06:40 (BOS)Boston Logan International Airport
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08:15 (MDW)Chicago Midway Airport
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(WN 3047)Boeing 737 Max 8 Passenger - 2h 35m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 Max 8 Passenger
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07:00 - 08:40BOS - MDW
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07:00 (BOS)Boston Logan International Airport
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08:40 (MDW)Chicago Midway Airport
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(WN 3047)Boeing 737 Max 8 Passenger - 2h 40m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
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07:00 - 09:10BOS - ORD
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07:00 (BOS)Boston Logan International Airport
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09:10 (ORD)Chicago O'Hare International Airport
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JetBlue Airways (B6 311)Embraer Emb E90 - 3h 10m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Embraer Emb E90
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07:05 - 09:11BOS - ORD
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07:05 (BOS)Boston Logan International Airport
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09:11 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 1088)Airbus A220 100 Passenger - 3h 06m
- Direct
-
- M
- T
- W
- T
- F
- -
- -
- Airbus A220 100 Passenger
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07:05 - 08:45BOS - MDW
-
07:05 (BOS)Boston Logan International Airport
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08:45 (MDW)Chicago Midway Airport
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(WN 3047)Boeing 737 Max 8 Passenger - 2h 40m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
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07:10 - 08:50BOS - MDW
-
07:10 (BOS)Boston Logan International Airport
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08:50 (MDW)Chicago Midway Airport
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(WN 3047)Boeing 737 Max 8 Passenger - 2h 40m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
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07:40 - 09:15BOS - ORD
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07:40 (BOS)Boston Logan International Airport
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09:15 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1509)Boeing 737 Max 8 Passenger - 2h 35m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 Max 8 Passenger
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08:00 - 10:06BOS - ORD
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08:00 (BOS)Boston Logan International Airport
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10:06 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 1154)Airbus A220 100 Passenger - 3h 06m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Airbus A220 100 Passenger
-
09:15 - 11:10BOS - ORD
-
09:15 (BOS)Boston Logan International Airport
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11:10 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1502)Boeing 737 800 - 2h 55m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
10:20 - 12:04BOS - ORD
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10:20 (BOS)Boston Logan International Airport
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12:04 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 408)Boeing 737 800 - 2h 44m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
10:30 - 12:33BOS - ORD
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10:30 (BOS)Boston Logan International Airport
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12:33 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 1429)Airbus A220 100 Passenger - 3h 03m
- Direct
-
- M
- T
- W
- T
- F
- -
- S
- Airbus A220 100 Passenger
-
10:45 - 12:20BOS - MDW
-
10:45 (BOS)Boston Logan International Airport
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12:20 (MDW)Chicago Midway Airport
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(WN 3048)Boeing 737 800 - 2h 35m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
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10:50 - 12:20BOS - MDW
-
10:50 (BOS)Boston Logan International Airport
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12:20 (MDW)Chicago Midway Airport
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(WN 3048)Boeing 737 700 - 2h 30m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
11:20 - 12:50BOS - MDW
-
11:20 (BOS)Boston Logan International Airport
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12:50 (MDW)Chicago Midway Airport
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(WN 3048)Boeing 737 Max 8 Passenger - 2h 30m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
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12:20 - 13:55BOS - MDW
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12:20 (BOS)Boston Logan International Airport
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13:55 (MDW)Chicago Midway Airport
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(WN 3048)Boeing 737 Max 8 Passenger - 2h 35m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 Max 8 Passenger
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12:25 - 14:20BOS - ORD
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12:25 (BOS)Boston Logan International Airport
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14:20 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1457)Boeing 737 800 - 2h 55m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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12:30 - 14:36BOS - ORD
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12:30 (BOS)Boston Logan International Airport
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14:36 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1732)Boeing 737 800 - 3h 06m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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13:00 - 15:03BOS - ORD
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13:00 (BOS)Boston Logan International Airport
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15:03 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 521)Airbus A220 100 Passenger - 3h 03m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Airbus A220 100 Passenger
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13:45 - 15:47BOS - ORD
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13:45 (BOS)Boston Logan International Airport
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15:47 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 2427)Airbus A220 100 Passenger - 3h 02m
- Direct
-
- M
- T
- W
- T
- F
- -
- S
- Airbus A220 100 Passenger
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14:15 - 16:10BOS - ORD
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14:15 (BOS)Boston Logan International Airport
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16:10 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1479)Boeing 737 800 - 2h 55m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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15:58 - 17:50BOS - ORD
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15:58 (BOS)Boston Logan International Airport
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17:50 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 3711)Embraer Emb 175 - 2h 52m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Embraer Emb 175
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16:20 - 17:55BOS - MDW
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16:20 (BOS)Boston Logan International Airport
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17:55 (MDW)Chicago Midway Airport
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(WN 3049)Boeing 737 800 - 2h 35m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
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16:30 - 18:17BOS - ORD
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16:30 (BOS)Boston Logan International Airport
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18:17 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1783)Boeing 737 900 - 2h 47m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 900
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16:50 - 18:30BOS - MDW
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16:50 (BOS)Boston Logan International Airport
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18:30 (MDW)Chicago Midway Airport
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(WN 3049)Boeing 737 Max 8 Passenger - 2h 40m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 Max 8 Passenger
-
16:55 - 18:35BOS - MDW
-
16:55 (BOS)Boston Logan International Airport
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18:35 (MDW)Chicago Midway Airport
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(WN 3049)Boeing 737 Max 8 Passenger - 2h 40m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
-
17:05 - 19:15BOS - ORD
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17:05 (BOS)Boston Logan International Airport
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19:15 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 742)Airbus A220 100 Passenger - 3h 10m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus A220 100 Passenger
-
17:43 - 19:40BOS - ORD
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17:43 (BOS)Boston Logan International Airport
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19:40 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1485)Boeing 737 800 - 2h 57m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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18:27 - 20:10BOS - ORD
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18:27 (BOS)Boston Logan International Airport
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20:10 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1150)Boeing 737 900 - 2h 43m
- Direct
-
- M
- T
- W
- T
- F
- -
- S
- Boeing 737 900
-
19:15 - 20:50BOS - MDW
-
19:15 (BOS)Boston Logan International Airport
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20:50 (MDW)Chicago Midway Airport
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(WN 5774)Boeing 737 800 - 2h 35m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
-
19:20 - 21:00BOS - MDW
-
19:20 (BOS)Boston Logan International Airport
-
21:00 (MDW)Chicago Midway Airport
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(WN 5774)Boeing 737 800 - 2h 40m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
Connecting Flights
-
20:15 - 22:00+ 1BOS - BNA22:40 - 00:10+ 1BNA - MDW
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20:15 (BOS)Boston Logan International Airport22:40 (BNA)Nashville Airport
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22:00 (BNA)Nashville Airport + 100:10 (MDW)Chicago Midway Airport
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(WN 794)Boeing 737 Max 8 Passenger (WN 5212)Boeing 737 700 - 4h 55m (40m)
- BNA Nashville 40m
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- -
- -
- -
- -
- -
- -
- S
-
05:20 - 07:00BOS - BNA08:15 - 10:00BNA - ORD
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05:20 (BOS)Boston Logan International Airport08:15 (BNA)Nashville Airport
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07:00 (BNA)Nashville Airport10:00 (ORD)Chicago O'Hare International Airport
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(WN 528)Boeing 737 800 (WN 3623)Boeing 737 700 - 5h 40m (1h 15m)
- BNA Nashville 1h 15m
-
- -
- -
- -
- -
- -
- -
- S
-
05:40 - 07:20BOS - BNA09:00 - 10:45BNA - ORD
-
05:40 (BOS)Boston Logan International Airport09:00 (BNA)Nashville Airport
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07:20 (BNA)Nashville Airport10:45 (ORD)Chicago O'Hare International Airport
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(WN 528)Boeing 737 800 (WN 510)Boeing 737 700 - 6h 05m (1h 40m)
- BNA Nashville 1h 40m
-
- M
- -
- -
- T
- F
- -
- -
-
05:45 - 07:25BOS - BNA09:45 - 11:15BNA - MDW
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05:45 (BOS)Boston Logan International Airport09:45 (BNA)Nashville Airport
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07:25 (BNA)Nashville Airport11:15 (MDW)Chicago Midway Airport
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(WN 528)Boeing 737 800 (WN 2119)Boeing 737 700 - 6h 30m (2h 20m)
- BNA Nashville 2h 20m
-
- -
- T
- W
- -
- -
- -
- -
-
05:45 - 07:25BOS - BNA09:00 - 10:45BNA - ORD
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05:45 (BOS)Boston Logan International Airport09:00 (BNA)Nashville Airport
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07:25 (BNA)Nashville Airport10:45 (ORD)Chicago O'Hare International Airport
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(WN 528)Boeing 737 800 (WN 510)Boeing 737 700 - 6h (1h 35m)
- BNA Nashville 1h 35m
-
- -
- T
- W
- -
- -
- -
- -
-
06:05 - 07:40BOS - BWI10:10 - 11:10BWI - MDW
-
06:05 (BOS)Boston Logan International Airport10:10 (BWI)Baltimore Washington International Airport
-
07:40 (BWI)Baltimore Washington International Airport11:10 (MDW)Chicago Midway Airport
-
(WN 489)Boeing 737 Max 8 Passenger (WN 1930)Boeing 737 Max 8 Passenger - 6h 05m (2h 30m)
- BWI Baltimore 2h 30m
-
- -
- T
- W
- -
- -
- -
- -
-
06:05 - 07:40BOS - BWI08:40 - 10:00BWI - ORD
-
06:05 (BOS)Boston Logan International Airport08:40 (BWI)Baltimore Washington International Airport
-
07:40 (BWI)Baltimore Washington International Airport10:00 (ORD)Chicago O'Hare International Airport
-
(WN 489)Boeing 737 Max 8 Passenger (WN 3626)Boeing 737 700 - 4h 55m (1h)
- BWI Baltimore 1h
-
- -
- T
- W
- -
- -
- -
- -
-
06:05 - 07:40BOS - BWI08:40 - 10:00BWI - ORD
-
06:05 (BOS)Boston Logan International Airport08:40 (BWI)Baltimore Washington International Airport
-
07:40 (BWI)Baltimore Washington International Airport10:00 (ORD)Chicago O'Hare International Airport
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(WN 489)Boeing 737 Max 8 Passenger (WN 3626)Boeing 737 800 - 4h 55m (1h)
- BWI Baltimore 1h
-
- M
- -
- -
- T
- F
- -
- -
-
08:05 - 09:55BOS - STL12:20 - 13:25STL - MDW
-
08:05 (BOS)Boston Logan International Airport12:20 (STL)St Louis Lambert Intl Airport
-
09:55 (STL)St Louis Lambert Intl Airport13:25 (MDW)Chicago Midway Airport
-
(WN 5577)Boeing 737 800 (WN 1268)Boeing 737 700 - 6h 20m (2h 25m)
- STL Saint Louis 2h 25m
-
- -
- T
- W
- -
- -
- -
- -
-
08:15 - 09:50BOS - BWI11:55 - 13:05BWI - ORD
-
08:15 (BOS)Boston Logan International Airport11:55 (BWI)Baltimore Washington International Airport
-
09:50 (BWI)Baltimore Washington International Airport13:05 (ORD)Chicago O'Hare International Airport
-
(WN 1739)Boeing 737 700 (WN 1090)Boeing 737 700 - 5h 50m (2h 05m)
- BWI Baltimore 2h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
08:30 - 10:00BOS - BWI13:05 - 14:05BWI - MDW
-
08:30 (BOS)Boston Logan International Airport13:05 (BWI)Baltimore Washington International Airport
-
10:00 (BWI)Baltimore Washington International Airport14:05 (MDW)Chicago Midway Airport
-
(WN 900)Boeing 737 Max 8 Passenger (WN 5950)Boeing 737 800 - 6h 35m (3h 05m)
- BWI Baltimore 3h 05m
-
- -
- T
- W
- -
- -
- -
- -
-
09:30 - 11:05BOS - BWI13:15 - 14:15BWI - MDW
-
09:30 (BOS)Boston Logan International Airport13:15 (BWI)Baltimore Washington International Airport
-
11:05 (BWI)Baltimore Washington International Airport14:15 (MDW)Chicago Midway Airport
-
(WN 900)Boeing 737 800 (WN 5950)Boeing 737 Max 8 Passenger - 5h 45m (2h 10m)
- BWI Baltimore 2h 10m
-
- -
- -
- -
- -
- -
- -
- S
-
09:35 - 11:20BOS - BNA12:55 - 14:30BNA - MDW
-
09:35 (BOS)Boston Logan International Airport12:55 (BNA)Nashville Airport
-
11:20 (BNA)Nashville Airport14:30 (MDW)Chicago Midway Airport
-
(WN 528)Boeing 737 800 (WN 5597)Boeing 737 800 - 5h 55m (1h 35m)
- BNA Nashville 1h 35m
-
- -
- -
- -
- -
- -
- S
- -
-
10:25 - 11:55BOS - BWI13:45 - 14:45BWI - MDW
-
10:25 (BOS)Boston Logan International Airport13:45 (BWI)Baltimore Washington International Airport
-
11:55 (BWI)Baltimore Washington International Airport14:45 (MDW)Chicago Midway Airport
-
(WN 900)Boeing 737 Max 8 Passenger (WN 5950)Boeing 737 800 - 5h 20m (1h 50m)
- BWI Baltimore 1h 50m
-
- M
- -
- -
- T
- F
- -
- -
-
11:50 - 13:20BOS - BWI16:00 - 17:00BWI - MDW
-
11:50 (BOS)Boston Logan International Airport16:00 (BWI)Baltimore Washington International Airport
-
13:20 (BWI)Baltimore Washington International Airport17:00 (MDW)Chicago Midway Airport
-
(WN 2676)Boeing 737 800 (WN 2136)Boeing 737 800 - 6h 10m (2h 40m)
- BWI Baltimore 2h 40m
-
- -
- -
- -
- -
- -
- S
- -
-
11:50 - 13:20BOS - BWI15:10 - 16:25BWI - ORD
-
11:50 (BOS)Boston Logan International Airport15:10 (BWI)Baltimore Washington International Airport
-
13:20 (BWI)Baltimore Washington International Airport16:25 (ORD)Chicago O'Hare International Airport
-
(WN 2676)Boeing 737 800 (WN 3191)Boeing 737 700 - 5h 35m (1h 50m)
- BWI Baltimore 1h 50m
-
- -
- -
- -
- -
- -
- S
- -
-
12:40 - 14:15BOS - BWI16:40 - 17:45BWI - MDW
-
12:40 (BOS)Boston Logan International Airport16:40 (BWI)Baltimore Washington International Airport
-
14:15 (BWI)Baltimore Washington International Airport17:45 (MDW)Chicago Midway Airport
-
(WN 579)Boeing 737 700 (WN 2136)Boeing 737 800 - 6h 05m (2h 25m)
- BWI Baltimore 2h 25m
-
- -
- T
- W
- -
- -
- -
- -
-
12:55 - 14:45BOS - STL15:50 - 16:55STL - MDW
-
12:55 (BOS)Boston Logan International Airport15:50 (STL)St Louis Lambert Intl Airport
-
14:45 (STL)St Louis Lambert Intl Airport16:55 (MDW)Chicago Midway Airport
-
(WN 4614)Boeing 737 800 (WN 3242)Boeing 737 700 - 5h (1h 05m)
- STL Saint Louis 1h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
12:55 - 14:45BOS - STL17:10 - 18:15STL - MDW
-
12:55 (BOS)Boston Logan International Airport17:10 (STL)St Louis Lambert Intl Airport
-
14:45 (STL)St Louis Lambert Intl Airport18:15 (MDW)Chicago Midway Airport
-
(WN 4614)Boeing 737 Max 8 Passenger (WN 3244)Boeing 737 800 - 6h 20m (2h 25m)
- STL Saint Louis 2h 25m
-
- -
- -
- -
- -
- -
- S
- -
-
13:00 - 14:35BOS - BWI16:40 - 17:40BWI - MDW
-
13:00 (BOS)Boston Logan International Airport16:40 (BWI)Baltimore Washington International Airport
-
14:35 (BWI)Baltimore Washington International Airport17:40 (MDW)Chicago Midway Airport
-
(WN 579)Boeing 737 800 (WN 2136)Boeing 737 Max 8 Passenger - 5h 40m (2h 05m)
- BWI Baltimore 2h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
13:15 - 14:45BOS - BWI15:35 - 16:35BWI - MDW
-
13:15 (BOS)Boston Logan International Airport15:35 (BWI)Baltimore Washington International Airport
-
14:45 (BWI)Baltimore Washington International Airport16:35 (MDW)Chicago Midway Airport
-
(WN 579)Boeing 737 Max 8 Passenger (WN 2136)Boeing 737 Max 8 Passenger - 4h 20m (50m)
- BWI Baltimore 50m
-
- -
- -
- -
- -
- -
- -
- S
-
13:55 - 15:50BOS - STL17:25 - 18:30STL - MDW
-
13:55 (BOS)Boston Logan International Airport17:25 (STL)St Louis Lambert Intl Airport
-
15:50 (STL)St Louis Lambert Intl Airport18:30 (MDW)Chicago Midway Airport
-
(WN 4614)Boeing 737 700 (WN 5687)Boeing 737 800 - 5h 35m (1h 35m)
- STL Saint Louis 1h 35m
-
- -
- T
- W
- -
- -
- -
- -
-
15:35 - 17:05BOS - BWI18:45 - 19:45BWI - MDW
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15:35 (BOS)Boston Logan International Airport18:45 (BWI)Baltimore Washington International Airport
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17:05 (BWI)Baltimore Washington International Airport19:45 (MDW)Chicago Midway Airport
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(WN 909)Boeing 737 700 (WN 1789)Boeing 737 Max 8 Passenger - 5h 10m (1h 40m)
- BWI Baltimore 1h 40m
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- -
- -
- -
- -
- S
- -
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16:15 - 17:50BOS - BWI20:20 - 21:25BWI - MDW
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16:15 (BOS)Boston Logan International Airport20:20 (BWI)Baltimore Washington International Airport
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17:50 (BWI)Baltimore Washington International Airport21:25 (MDW)Chicago Midway Airport
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(WN 2922)Boeing 737 700 (WN 3059)Boeing 737 700 - 6h 10m (2h 30m)
- BWI Baltimore 2h 30m
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- -
- T
- W
- -
- -
- -
- -
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17:40 - 19:15BOS - BWI21:00 - 22:00BWI - MDW
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17:40 (BOS)Boston Logan International Airport21:00 (BWI)Baltimore Washington International Airport
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19:15 (BWI)Baltimore Washington International Airport22:00 (MDW)Chicago Midway Airport
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(WN 580)Boeing 737 800 (WN 3059)Boeing 737 Max 8 Passenger - 5h 20m (1h 45m)
- BWI Baltimore 1h 45m
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- M
- -
- -
- T
- F
- -
- -
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17:40 - 19:25BOS - BWI21:55 - 22:55BWI - MDW
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17:40 (BOS)Boston Logan International Airport21:55 (BWI)Baltimore Washington International Airport
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19:25 (BWI)Baltimore Washington International Airport22:55 (MDW)Chicago Midway Airport
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(WN 580)Boeing 737 800 (WN 2775)Boeing 737 700 - 6h 15m (2h 30m)
- BWI Baltimore 2h 30m
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- -
- -
- -
- -
- -
- -
- S
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17:40 - 19:15BOS - BWI21:10 - 22:20BWI - ORD
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17:40 (BOS)Boston Logan International Airport21:10 (BWI)Baltimore Washington International Airport
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19:15 (BWI)Baltimore Washington International Airport22:20 (ORD)Chicago O'Hare International Airport
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(WN 580)Boeing 737 800 (WN 5289)Boeing 737 Max 8 Passenger - 5h 40m (1h 55m)
- BWI Baltimore 1h 55m
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- M
- -
- -
- T
- F
- -
- -
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17:40 - 19:25BOS - BWI21:10 - 22:20BWI - ORD
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17:40 (BOS)Boston Logan International Airport21:10 (BWI)Baltimore Washington International Airport
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19:25 (BWI)Baltimore Washington International Airport22:20 (ORD)Chicago O'Hare International Airport
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(WN 580)Boeing 737 800 (WN 5289)Boeing 737 800 - 5h 40m (1h 45m)
- BWI Baltimore 1h 45m
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- -
- -
- -
- -
- -
- -
- S
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18:00 - 19:35BOS - BWI21:10 - 22:20BWI - ORD
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18:00 (BOS)Boston Logan International Airport21:10 (BWI)Baltimore Washington International Airport
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19:35 (BWI)Baltimore Washington International Airport22:20 (ORD)Chicago O'Hare International Airport
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(WN 580)Boeing 737 Max 8 Passenger (WN 5289)Boeing 737 700 - 5h 20m (1h 35m)
- BWI Baltimore 1h 35m
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- -
- T
- W
- -
- -
- -
- -
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18:00 - 19:35BOS - BWI20:20 - 21:25BWI - MDW
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18:00 (BOS)Boston Logan International Airport20:20 (BWI)Baltimore Washington International Airport
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19:35 (BWI)Baltimore Washington International Airport21:25 (MDW)Chicago Midway Airport
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(WN 580)Boeing 737 Max 8 Passenger (WN 3059)Boeing 737 700 - 4h 25m (45m)
- BWI Baltimore 45m
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- -
- T
- W
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- -
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- -
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18:35 - 20:35BOS - STL21:30 - 22:35STL - MDW
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18:35 (BOS)Boston Logan International Airport21:30 (STL)St Louis Lambert Intl Airport
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20:35 (STL)St Louis Lambert Intl Airport22:35 (MDW)Chicago Midway Airport
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(WN 4615)Boeing 737 Max 8 Passenger (WN 3244)Boeing 737 Max 8 Passenger - 5h (55m)
- STL Saint Louis 55m
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- -
- T
- W
- -
- -
- -
- -
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18:55 - 20:40BOS - BNA21:30 - 23:00BNA - MDW
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18:55 (BOS)Boston Logan International Airport21:30 (BNA)Nashville Airport
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20:40 (BNA)Nashville Airport23:00 (MDW)Chicago Midway Airport
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(WN 532)Boeing 737 800 (WN 3046)Boeing 737 Max 8 Passenger - 5h 05m (50m)
- BNA Nashville 50m
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- -
- T
- W
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19:15 - 21:00BOS - BNA21:50 - 23:25BNA - MDW
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19:15 (BOS)Boston Logan International Airport21:50 (BNA)Nashville Airport
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21:00 (BNA)Nashville Airport23:25 (MDW)Chicago Midway Airport
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(WN 532)Boeing 737 800 (WN 3046)Boeing 737 700 - 5h 10m (50m)
- BNA Nashville 50m
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- M
- -
- -
- T
- F
- -
- -
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19:50 - 21:45BOS - STL22:50 - 23:55STL - MDW
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19:50 (BOS)Boston Logan International Airport22:50 (STL)St Louis Lambert Intl Airport
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21:45 (STL)St Louis Lambert Intl Airport23:55 (MDW)Chicago Midway Airport
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(WN 4615)Boeing 737 Max 8 Passenger (WN 3244)Boeing 737 800 - 5h 05m (1h 05m)
- STL Saint Louis 1h 05m
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- -
- -
- -
- -
- -
- -
- S
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What’s the fastest flight time from Boston to Chicago?
The fastest flight time for direct flights from Boston to Chicago is 2 hours 30 minutes. Check latest flight schedules & prices on Wego.
What’s the most popular airline flying from Boston to Chicago?
The most popular airline flying from Boston to Chicago is American Airlines. Find the latest flight deals on Wego.
How far is Chicago from Boston?
The flight distance between Boston and Chicago is 1366km. Check all available flights on Wego.
When is the earliest and latest flight of the day?
The earliest flight of the day departs at 05:20. The last flight of the day departs at 20:15. See the full list of flight times on Wego.
How many airlines offer direct flights from Boston to Chicago?
There are 5 airlines that offer direct flights from Boston to Chicago. Find out the list of airlines on Wego.
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Popular Airlines flying from Boston to Chicago
Popular destinations from Chicago
Popular destinations from Boston
Popular Hotels in Chicago
- Clarion Inn Elmhurst - Oak Brook near I-88, I-290, I-294
- The Royal Sonesta Chicago Downtown
- Club Quarters Hotel, Central Loop, Chicago
- The Ritz-Carlton, Chicago
- Fairmont Chicago at Millennium Park Gold Experience
- Swissôtel Chicago
- Pendry Chicago
- Hotel Felix Chicago
- Hotel Saint Clair
- Best Western River North Hotel