Fare Guide
Estimated lowest fares found within 7 days
The cheapest airline(s) flying from Chicago to Boston is Spirit Airlines.
Travel Period: June 2024 - May 2025
The cheapest month(s) to fly from Chicago to Boston is June.
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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
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May 2025
The cheapest day(s) of the week to fly from Chicago to Boston 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
The cheapest time of the day to fly from Chicago to Boston is in the evening.
Flight Schedules
Last Updated: Thu, 2 May, 2024
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Total Duration
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Availability
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19:15 - 22:30MDW - BOS
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19:15 (MDW)Chicago Midway Airport
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22:30 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 2383)Boeing 737 Max 8 Passenger - 2h 15m
- Direct
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- -
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- -
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- Boeing 737 Max 8 Passenger
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19:15 - 22:47ORD - BOS
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19:15 (ORD)Chicago O'Hare International Airport
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22:47 (BOS)Boston Logan International Airport
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Delta Air Lines (DL 2346)Airbus A220 100 Passenger - 2h 32m
- Direct
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- M
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- -
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- Airbus A220 100 Passenger
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19:45 - 23:00MDW - BOS
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19:45 (MDW)Chicago Midway Airport
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23:00 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 2383)Boeing 737 800 - 2h 15m
- Direct
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- M
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- F
- -
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- Boeing 737 800
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20:20 - 23:40ORD - BOS
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20:20 (ORD)Chicago O'Hare International Airport
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23:40 (BOS)Boston Logan International Airport
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American Airlines (AA 2682)Boeing 737 800 - 2h 20m
- Direct
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- M
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- T
- F
- S
- S
- Boeing 737 800
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20:30 - 23:45MDW - BOS
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20:30 (MDW)Chicago Midway Airport
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23:45 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 2383)Boeing 737 800 - 2h 15m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
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21:05 - 00:19+ 1ORD - BOS
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21:05 (ORD)Chicago O'Hare International Airport
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00:19 (BOS)Boston Logan International Airport + 1
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United Airlines (UA 2627)Boeing 737 800 - 2h 14m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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06:15 - 09:30MDW - BOS
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06:15 (MDW)Chicago Midway Airport
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09:30 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 862)Boeing 737 Max 8 Passenger - 2h 15m
- Direct
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- M
- -
- -
- T
- F
- -
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- Boeing 737 Max 8 Passenger
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06:30 - 09:56ORD - BOS
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06:30 (ORD)Chicago O'Hare International Airport
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09:56 (BOS)Boston Logan International Airport
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American Airlines (AA 3710)Embraer Emb 175 - 2h 26m
- Direct
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- M
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- Embraer Emb 175
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07:00 - 10:27ORD - BOS
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07:00 (ORD)Chicago O'Hare International Airport
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10:27 (BOS)Boston Logan International Airport
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Delta Air Lines (DL 1411)Airbus A220 100 Passenger - 2h 27m
- Direct
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- M
- T
- W
- T
- F
- -
- -
- Airbus A220 100 Passenger
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07:00 - 10:27ORD - BOS
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07:00 (ORD)Chicago O'Hare International Airport
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10:27 (BOS)Boston Logan International Airport
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Delta Air Lines (DL 1371)Airbus A220 100 Passenger - 2h 27m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Airbus A220 100 Passenger
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07:00 - 10:15MDW - BOS
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07:00 (MDW)Chicago Midway Airport
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10:15 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 862)Boeing 737 700 - 2h 15m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
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07:15 - 10:30MDW - BOS
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07:15 (MDW)Chicago Midway Airport
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10:30 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 862)Boeing 737 Max 8 Passenger - 2h 15m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
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07:45 - 11:06ORD - BOS
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07:45 (ORD)Chicago O'Hare International Airport
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11:06 (BOS)Boston Logan International Airport
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United Airlines (UA 1803)Boeing 737 800 - 2h 21m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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08:20 - 11:38ORD - BOS
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08:20 (ORD)Chicago O'Hare International Airport
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11:38 (BOS)Boston Logan International Airport
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American Airlines (AA 1457)Boeing 737 800 - 2h 18m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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08:40 - 12:04ORD - BOS
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08:40 (ORD)Chicago O'Hare International Airport
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12:04 (BOS)Boston Logan International Airport
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JetBlue Airways (B6 312)Airbus A220 300 - 2h 24m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Airbus A220 300
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08:50 - 12:10MDW - BOS
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08:50 (MDW)Chicago Midway Airport
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12:10 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 5802)Boeing 737 Max 8 Passenger - 2h 20m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 Max 8 Passenger
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08:52 - 12:11ORD - BOS
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08:52 (ORD)Chicago O'Hare International Airport
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12:11 (BOS)Boston Logan International Airport
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United Airlines (UA 1495)Boeing 737 700 - 2h 19m
- Direct
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- M
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- W
- T
- F
- -
- S
- Boeing 737 700
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09:00 - 12:15MDW - BOS
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09:00 (MDW)Chicago Midway Airport
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12:15 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 5802)Boeing 737 800 - 2h 15m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
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09:55 - 13:13ORD - BOS
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09:55 (ORD)Chicago O'Hare International Airport
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13:13 (BOS)Boston Logan International Airport
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American Airlines (AA 1479)Boeing 737 800 - 2h 18m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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10:15 - 13:42ORD - BOS
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10:15 (ORD)Chicago O'Hare International Airport
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13:42 (BOS)Boston Logan International Airport
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Delta Air Lines (DL 1088)Airbus A220 100 Passenger - 2h 27m
- Direct
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- M
- T
- W
- T
- F
- -
- S
- Airbus A220 100 Passenger
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10:51 - 14:11ORD - BOS
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10:51 (ORD)Chicago O'Hare International Airport
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14:11 (BOS)Boston Logan International Airport
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United Airlines (UA 691)Boeing 737 800 - 2h 20m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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11:35 - 14:55MDW - BOS
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11:35 (MDW)Chicago Midway Airport
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14:55 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 745)Boeing 737 Max 8 Passenger - 2h 20m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
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12:00 - 15:27ORD - BOS
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12:00 (ORD)Chicago O'Hare International Airport
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15:27 (BOS)Boston Logan International Airport
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Delta Air Lines (DL 1154)Airbus A220 100 Passenger - 2h 27m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Airbus A220 100 Passenger
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12:30 - 15:50MDW - BOS
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12:30 (MDW)Chicago Midway Airport
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15:50 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 2383)Boeing 737 800 - 2h 20m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 800
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13:20 - 16:39ORD - BOS
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13:20 (ORD)Chicago O'Hare International Airport
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16:39 (BOS)Boston Logan International Airport
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American Airlines (AA 1485)Boeing 737 800 - 2h 19m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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13:55 - 17:15MDW - BOS
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13:55 (MDW)Chicago Midway Airport
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17:15 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 745)Boeing 737 Max 8 Passenger - 2h 20m
- Direct
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- -
- T
- W
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- -
- -
- -
- Boeing 737 Max 8 Passenger
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14:00 - 17:20ORD - BOS
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14:00 (ORD)Chicago O'Hare International Airport
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17:20 (BOS)Boston Logan International Airport
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United Airlines (UA 378)Boeing 737 900 - 2h 20m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 900
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14:15 - 17:47ORD - BOS
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14:15 (ORD)Chicago O'Hare International Airport
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17:47 (BOS)Boston Logan International Airport
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Delta Air Lines (DL 1429)Airbus A220 100 Passenger - 2h 32m
- Direct
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- M
- T
- W
- T
- F
- -
- S
- Airbus A220 100 Passenger
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16:00 - 19:15MDW - BOS
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16:00 (MDW)Chicago Midway Airport
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19:15 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 745)Boeing 737 700 - 2h 15m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
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16:50 - 20:06ORD - BOS
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16:50 (ORD)Chicago O'Hare International Airport
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20:06 (BOS)Boston Logan International Airport
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American Airlines (AA 1461)Boeing 737 800 - 2h 16m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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17:05 - 20:20MDW - BOS
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17:05 (MDW)Chicago Midway Airport
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20:20 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 745)Boeing 737 800 - 2h 15m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 800
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17:30 - 21:00ORD - BOS
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17:30 (ORD)Chicago O'Hare International Airport
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21:00 (BOS)Boston Logan International Airport
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Delta Air Lines (DL 2427)Airbus A220 100 Passenger - 2h 30m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Airbus A220 100 Passenger
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17:50 - 21:10MDW - BOS
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17:50 (MDW)Chicago Midway Airport
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21:10 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 998)Boeing 737 800 - 2h 20m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
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17:57 - 21:11ORD - BOS
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17:57 (ORD)Chicago O'Hare International Airport
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21:11 (BOS)Boston Logan International Airport
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United Airlines (UA 1568)Boeing 737 900 - 2h 14m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 900
-
18:25 - 21:53ORD - BOS
-
18:25 (ORD)Chicago O'Hare International Airport
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21:53 (BOS)Boston Logan International Airport
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American Airlines (AA 1033)Boeing 737 Max 8 Passenger - 2h 28m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 Max 8 Passenger
Connecting Flights
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05:55 - 07:05MDW - STL08:00 - 11:35STL - BOS
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05:55 (MDW)Chicago Midway Airport08:00 (STL)St Louis Lambert Intl Airport
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07:05 (STL)St Louis Lambert Intl Airport11:35 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 5846)Boeing 737 Max 8 Passenger Southwest Airlines (WN 949)Boeing 737 Max 8 Passenger - 4h 40m (55m)
- STL Saint Louis 55m
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- -
- -
- -
- -
- -
- S
- -
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07:15 - 08:45ORD - BNA10:10 - 13:40BNA - BOS
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07:15 (ORD)Chicago O'Hare International Airport10:10 (BNA)Nashville Airport
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08:45 (BNA)Nashville Airport13:40 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 658)Boeing 737 Max 8 Passenger Southwest Airlines (WN 1535)Boeing 737 Max 8 Passenger - 5h 25m (1h 25m)
- BNA Nashville 1h 25m
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- -
- -
- -
- -
- -
- -
- S
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08:00 - 09:25MDW - BNA10:25 - 13:55BNA - BOS
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08:00 (MDW)Chicago Midway Airport10:25 (BNA)Nashville Airport
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09:25 (BNA)Nashville Airport13:55 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 433)Boeing 737 Max 8 Passenger Southwest Airlines (WN 1535)Boeing 737 Max 8 Passenger - 4h 55m (1h)
- BNA Nashville 1h
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- M
- -
- -
- T
- F
- -
- -
-
08:15 - 11:10MDW - BWI12:30 - 13:55BWI - BOS
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08:15 (MDW)Chicago Midway Airport12:30 (BWI)Baltimore Washington International Airport
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11:10 (BWI)Baltimore Washington International Airport13:55 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 5903)Boeing 737 800 Southwest Airlines (WN 5279)Boeing 737 800 - 4h 40m (1h 20m)
- BWI Baltimore 1h 20m
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- M
- -
- -
- T
- F
- -
- -
-
08:35 - 11:30MDW - BWI14:10 - 15:35BWI - BOS
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08:35 (MDW)Chicago Midway Airport14:10 (BWI)Baltimore Washington International Airport
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11:30 (BWI)Baltimore Washington International Airport15:35 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 5903)Boeing 737 700 Southwest Airlines (WN 5887)Boeing 737 700 - 6h (2h 40m)
- BWI Baltimore 2h 40m
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- -
- T
- W
- -
- -
- -
- -
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10:05 - 11:30MDW - BNA12:25 - 15:55BNA - BOS
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10:05 (MDW)Chicago Midway Airport12:25 (BNA)Nashville Airport
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11:30 (BNA)Nashville Airport15:55 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 433)Boeing 737 800 Southwest Airlines (WN 1535)Boeing 737 Max 8 Passenger - 4h 50m (55m)
- BNA Nashville 55m
-
- -
- -
- -
- -
- -
- S
- -
-
10:35 - 13:20MDW - BWI14:10 - 15:35BWI - BOS
-
10:35 (MDW)Chicago Midway Airport14:10 (BWI)Baltimore Washington International Airport
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13:20 (BWI)Baltimore Washington International Airport15:35 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 575)Boeing 737 Max 8 Passenger Southwest Airlines (WN 5887)Boeing 737 700 - 4h (50m)
- BWI Baltimore 50m
-
- -
- T
- W
- -
- -
- -
- -
-
11:25 - 12:35MDW - STL14:55 - 18:30STL - BOS
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11:25 (MDW)Chicago Midway Airport14:55 (STL)St Louis Lambert Intl Airport
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12:35 (STL)St Louis Lambert Intl Airport18:30 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 3021)Boeing 737 700 Southwest Airlines (WN 186)Boeing 737 800 - 6h 05m (2h 20m)
- STL Saint Louis 2h 20m
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- M
- -
- -
- T
- F
- -
- -
-
11:25 - 14:15ORD - BWI15:20 - 16:50BWI - BOS
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11:25 (ORD)Chicago O'Hare International Airport15:20 (BWI)Baltimore Washington International Airport
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14:15 (BWI)Baltimore Washington International Airport16:50 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 5932)Boeing 737 700 Southwest Airlines (WN 735)Boeing 737 800 - 4h 25m (1h 05m)
- BWI Baltimore 1h 05m
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- M
- -
- -
- T
- F
- -
- -
-
11:25 - 14:15ORD - BWI17:05 - 18:35BWI - BOS
-
11:25 (ORD)Chicago O'Hare International Airport17:05 (BWI)Baltimore Washington International Airport
-
14:15 (BWI)Baltimore Washington International Airport18:35 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 5932)Boeing 737 700 Southwest Airlines (WN 671)Boeing 737 800 - 6h 10m (2h 50m)
- BWI Baltimore 2h 50m
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- M
- -
- -
- T
- F
- -
- -
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12:05 - 13:15MDW - STL14:05 - 17:35STL - BOS
-
12:05 (MDW)Chicago Midway Airport14:05 (STL)St Louis Lambert Intl Airport
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13:15 (STL)St Louis Lambert Intl Airport17:35 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 3279)Boeing 737 700 Southwest Airlines (WN 186)Boeing 737 Max 8 Passenger - 4h 30m (50m)
- STL Saint Louis 50m
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- -
- T
- W
- -
- -
- -
- -
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12:15 - 15:05ORD - BWI16:40 - 18:05BWI - BOS
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12:15 (ORD)Chicago O'Hare International Airport16:40 (BWI)Baltimore Washington International Airport
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15:05 (BWI)Baltimore Washington International Airport18:05 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 5932)Boeing 737 800 Southwest Airlines (WN 671)Boeing 737 800 - 4h 50m (1h 35m)
- BWI Baltimore 1h 35m
-
- -
- T
- W
- -
- -
- -
- -
-
12:35 - 15:25MDW - BWI17:05 - 18:35BWI - BOS
-
12:35 (MDW)Chicago Midway Airport17:05 (BWI)Baltimore Washington International Airport
-
15:25 (BWI)Baltimore Washington International Airport18:35 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 1015)Boeing 737 Max 8 Passenger Southwest Airlines (WN 671)Boeing 737 800 - 5h (1h 40m)
- BWI Baltimore 1h 40m
-
- M
- -
- -
- T
- F
- -
- -
-
12:50 - 15:40MDW - BWI17:35 - 19:05BWI - BOS
-
12:50 (MDW)Chicago Midway Airport17:35 (BWI)Baltimore Washington International Airport
-
15:40 (BWI)Baltimore Washington International Airport19:05 (BOS)Boston Logan International Airport
-
Southwest Airlines (WN 1015)Boeing 737 800 Southwest Airlines (WN 1004)Boeing 737 Max 8 Passenger - 5h 15m (1h 55m)
- BWI Baltimore 1h 55m
-
- -
- -
- -
- -
- -
- -
- S
-
13:00 - 14:25MDW - BNA16:00 - 19:30BNA - BOS
-
13:00 (MDW)Chicago Midway Airport16:00 (BNA)Nashville Airport
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14:25 (BNA)Nashville Airport19:30 (BOS)Boston Logan International Airport
-
Southwest Airlines (WN 2942)Boeing 737 Max 8 Passenger Southwest Airlines (WN 5459)Boeing 737 Max 8 Passenger - 5h 30m (1h 35m)
- BNA Nashville 1h 35m
-
- -
- -
- -
- -
- -
- -
- S
-
13:45 - 16:35MDW - BWI18:10 - 19:40BWI - BOS
-
13:45 (MDW)Chicago Midway Airport18:10 (BWI)Baltimore Washington International Airport
-
16:35 (BWI)Baltimore Washington International Airport19:40 (BOS)Boston Logan International Airport
-
Southwest Airlines (WN 1015)Boeing 737 Max 8 Passenger Southwest Airlines (WN 1004)Boeing 737 Max 8 Passenger - 4h 55m (1h 35m)
- BWI Baltimore 1h 35m
-
- -
- T
- W
- -
- -
- -
- -
-
13:55 - 15:05MDW - STL17:10 - 20:40STL - BOS
-
13:55 (MDW)Chicago Midway Airport17:10 (STL)St Louis Lambert Intl Airport
-
15:05 (STL)St Louis Lambert Intl Airport20:40 (BOS)Boston Logan International Airport
-
Southwest Airlines (WN 5388)Boeing 737 700 Southwest Airlines (WN 186)Boeing 737 Max 8 Passenger - 5h 45m (2h 05m)
- STL Saint Louis 2h 05m
-
- -
- -
- -
- -
- -
- S
- -
-
14:50 - 17:40MDW - BWI19:40 - 21:05BWI - BOS
-
14:50 (MDW)Chicago Midway Airport19:40 (BWI)Baltimore Washington International Airport
-
17:40 (BWI)Baltimore Washington International Airport21:05 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 1833)Boeing 737 700 Southwest Airlines (WN 5824)Boeing 737 800 - 5h 15m (2h)
- BWI Baltimore 2h
-
- -
- -
- -
- -
- -
- -
- S
-
16:30 - 19:15MDW - BWI21:55 - 23:20BWI - BOS
-
16:30 (MDW)Chicago Midway Airport21:55 (BWI)Baltimore Washington International Airport
-
19:15 (BWI)Baltimore Washington International Airport23:20 (BOS)Boston Logan International Airport
-
Southwest Airlines (WN 1833)Boeing 737 Max 8 Passenger Southwest Airlines (WN 738)Boeing 737 800 - 5h 50m (2h 40m)
- BWI Baltimore 2h 40m
-
- M
- -
- -
- T
- F
- -
- -
-
17:15 - 20:00MDW - BWI21:50 - 23:15BWI - BOS
-
17:15 (MDW)Chicago Midway Airport21:50 (BWI)Baltimore Washington International Airport
-
20:00 (BWI)Baltimore Washington International Airport23:15 (BOS)Boston Logan International Airport
-
Southwest Airlines (WN 1833)Boeing 737 800 Southwest Airlines (WN 738)Boeing 737 Max 8 Passenger - 5h (1h 50m)
- BWI Baltimore 1h 50m
-
- -
- -
- -
- -
- -
- S
- -
-
17:25 - 20:20ORD - BWI21:55 - 23:20BWI - BOS
-
17:25 (ORD)Chicago O'Hare International Airport21:55 (BWI)Baltimore Washington International Airport
-
20:20 (BWI)Baltimore Washington International Airport23:20 (BOS)Boston Logan International Airport
-
Southwest Airlines (WN 1773)Boeing 737 800 Southwest Airlines (WN 738)Boeing 737 800 - 4h 55m (1h 35m)
- BWI Baltimore 1h 35m
-
- M
- -
- -
- T
- F
- -
- -
-
18:25 - 19:50+ 1MDW - BNA21:15 - 00:45+ 1BNA - BOS
-
18:25 (MDW)Chicago Midway Airport21:15 (BNA)Nashville Airport
-
19:50 (BNA)Nashville Airport + 100:45 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 3207)Boeing 737 Max 8 Passenger Southwest Airlines (WN 1343)Boeing 737 Max 8 Passenger - 5h 20m (1h 25m)
- BNA Nashville 1h 25m
-
- -
- -
- -
- -
- -
- -
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18:55 - 20:25+ 1ORD - BNA21:15 - 00:45+ 1BNA - BOS
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18:55 (ORD)Chicago O'Hare International Airport21:15 (BNA)Nashville Airport
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20:25 (BNA)Nashville Airport + 100:45 (BOS)Boston Logan International Airport
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Southwest Airlines (WN 5596)Boeing 737 Max 8 Passenger Southwest Airlines (WN 1343)Boeing 737 Max 8 Passenger - 4h 50m (50m)
- BNA Nashville 50m
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The fastest flight time for direct flights from Chicago to Boston is 2 hours 14 minutes. Check latest flight schedules & prices on Wego.
The flight distance between Chicago and Boston is 1366km. Check all available flights on Wego.
The earliest flight of the day departs at 05:55. The last flight of the day departs at 19:15. See the full list of flight times on Wego.
There are 5 airlines that offer direct flights from Chicago to Boston. Find out the list of airlines on Wego.