Cheap flights Boston — Chicago (BOS — CHI)

Good to know - Cheap tickets Boston — Chicago

Cheapest flight found $34
Minimal flight time 2h 25m
Flight distance 1366 km
Most popular airline American Airlines

Airfare Boston – Chicago by month

Here you can find out in what months how much a ticket Boston – Chicago costs to buy cheap plane tickets.

Month One-way Round-trip
September 2026
August 2026
July 2026
June 2026
May 2026
April 2026
March 2026
February 2026
January 2026
December 2025
November 2025
October 2025

Remember that the optimal time for booking air tickets is 59 days before the departure date, this is the average time at which air tickets were sold at the lowest prices.

Schedule of direct flights Boston — Chicago

Departure Arrival Flight days Flight Airlines Flight time Airports
04:45 06:28 sat 5X9715 UPS 2h 43m Logan International Airport — O'Hare International Airport Select dates
05:00 06:58 mon, tue, wed, thu, fri, sun AA3324 American Airlines 2h 58m Logan International Airport — O'Hare International Airport Select dates
05:00 06:51 daily AA3324 American Airlines 2h 51m Logan International Airport — O'Hare International Airport Select dates
05:15 07:00 thu, fri, sun WN2012 Southwest Airlines 2h 45m Logan International Airport — Chicago Midway International Airport Select dates
05:20 07:05 sat WN1430 Southwest Airlines 2h 45m Logan International Airport — Chicago Midway International Airport Select dates
05:24 07:25 daily AA3266 American Airlines 3h 1m Logan International Airport — O'Hare International Airport Select dates
05:28 07:24 daily AA3324 American Airlines 2h 56m Logan International Airport — O'Hare International Airport Select dates
05:30 07:15 mon, wed, thu WN1432 Southwest Airlines 2h 45m Logan International Airport — Chicago Midway International Airport Select dates
06:00 07:56 thu AA3324 American Airlines 2h 56m Logan International Airport — O'Hare International Airport Select dates
06:00 08:00 wed UA1414 United Airlines 3h 0m Logan International Airport — O'Hare International Airport Select dates
All routes

Flights Boston — Chicago

The selection of cheap flights Boston — Chicago

Here you can find and purchase the cheapest flights Boston — Chicago from $34 and Boston — Chicago — Boston from $36.

The price of the flight Boston — Chicago (United States) — Boston from $36 (round-trip).

The average price of the flight Boston — Chicago (United States) — Boston $246 (round-trip).

Low cost flights Boston — Chicago (BOS — CHI)

The distance between Boston and Chicago 849 miles (or 1366 kilometres).

The time difference between Boston and Chicago is 1 h.

Minimal flight time from Boston to Chicago 2h 25m.

LowCostClub always do a comparison of airfares Boston — Chicago with several airlines (include UPS, American Airlines, Southwest Airlines). They will always give you all available options so you can find the cheapest flight to Chicago. In addition, you can choose the platform where you want to place your orders. There are also special offers for air tickets Boston — Chicago. Last week, for instance, the cheapest round-trip prices stood at $36 while the cheapest one-way price that was available within the last week cost $34

Routes from nearby cities to Chicago

A flight from a neighbouring city can help you save money on plane tickets.

Most often, flights to Chicago are from Worcester. The cheapest plane ticket to Chicago can be bought from $53 with a departure from Hartford, which is also the nearest city from Boston.

Popular International routes from Boston

Boston — Moscow

Boston — Chania

Boston — Conakry

Boston — Cluj

Popular routes from Chicago

If you are going to fly from Chicago, then study the popular flights. The most popular flights from Chicago:

Popular domestic routes from Boston

FAQ about Boston — Chicago

Yes, they do: 5X9715, AA3324, WN2012, WN1430, AA3266, WN1432, UA1414, AA1328, AA4618, UA2467, DL2570, UA270, AA4404, B6311, 5X2019, WN3724, UA1349, DL5593, AA3799, AA3477, WN3771, WN1482, UA1314, AA4413, UA1732, DL2679, WN1484, AA1859, AA832, AA488, AA913, WN1081, AA3691, DL5722, DL5591, UA1301, AA4649, WN4496, AA2700, DL2646, AA4392, UA2040, B6811, WN1030, WN3969, WN1779, AA4385, AA4651, AA4683, UA1015, WN1436, AA1121, AA2500, AA1562, AA379, DL5596, DL5757, DL2676, WN3725, 5X9719, UA2229, AA3185, WN1488

Yes, you can fly from Boston to Chicago. Boston has 3 airports (Pease Air Force Base, Logan International Airport, Boston City Heliport) for flights. UPS, American Airlines, Southwest Airlines, United Airlines, Delta Air Lines, JetBlue depart from Boston on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through Aer Lingus, Aeromexico, Air Canada, Air France, Alaska Airlines, Allegiant Air, AlphaSky, Amazon Air, Arajet, Atlas Air, Austrian Airlines, avianca, British Airways, Cape Air, Cathay Pacific, Contour Aviation, Copa Airlines, Emirates, Etihad Airways, FedEx, Frontier (Miracle the Seagull Livery), GlobalX, Iberia Regional, Icelandair, Japan Airlines, Jet Linx Aviation, KLM, Korean Air, Lufthansa (Star Alliance Livery), NetJets, Porter, Porter Airlines Canada, Qatar Cargo, Republic Airways, SAS, Spirit Airlines, Sun Country Airlines, Swiss, TAP Air Portugal, Turkish Airlines, Virgin Atlantic, WestJet.

A direct flight lasts an average of 2h 25m, during which time the aircraft covers a distance of 1366 km.

The price of flights Boston — Chicago starts from $34.

Planes fly Boston — Chicago 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun

In Boston — Pease Air Force Base, Logan International Airport, Boston City Heliport. In Chicago — Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport.

The following flights fly between Boston and Chicago: 5X9715, AA3324, AA3324, WN2012, WN1430, AA3266, AA3324, WN1432, AA3324, UA1414, AA1328, UA1414, AA1328, AA4618, UA2467, UA2467, DL2570, AA4618, UA2467, UA270, UA2467, AA4404, B6311, 5X2019, WN3724, UA1349, DL5593, UA1349, AA3799, AA3477, AA3799, AA3477, WN3771, WN1482, UA1314, AA4413, AA4413, AA4413, AA3799, UA1732, UA1732, UA1732, UA1732, DL2679, WN1484, WN2012, AA1859, AA832, AA488, WN1432, AA913, WN1081, AA3691, DL5722, DL5591, UA1301, UA1301, AA4649, WN4496, AA2700, AA2700, DL2646, DL2646, DL2646, AA4392, DL2646, DL2646, UA2040, UA2040, AA4404, B6811, AA4404, WN1030, WN3969, B6811, WN1779, AA4385, B6811, AA4651, AA4683, UA1015, UA1015, WN1779, WN1436, AA1121, WN1030, AA2500, AA1562, AA2500, AA379, DL5596, DL5596, DL5757, DL2676, WN3725, 5X9719, 5X9715, UA2229, UA2229, AA3185, UA2229, WN1030, WN1488

High season is considered to be and the cheapest month is . Enter your preferred airports (or cities) and dates into the search form above to unlock the latest Boston — Chicago flight deals.

The following airlines have direct flights Boston — Chicago: UPS, American Airlines, Southwest Airlines, United Airlines, Delta Air Lines, JetBlue.

All the following airlines flights Boston — Chicago: Aer Lingus, Aeromexico, Air Canada, Air France, Alaska Airlines, Allegiant Air, AlphaSky, Amazon Air, American Airlines, Arajet, Atlas Air, Austrian Airlines, avianca, British Airways, Cape Air, Cathay Pacific, Contour Aviation, Copa Airlines, Delta Air Lines, Emirates, Etihad Airways, FedEx, Frontier (Miracle the Seagull Livery), GlobalX, Iberia Regional, Icelandair, Japan Airlines, Jet Linx Aviation, JetBlue, KLM, Korean Air, Lufthansa (Star Alliance Livery), NetJets, Porter, Porter Airlines Canada, Qatar Cargo, Republic Airways, SAS, Southwest Airlines, Spirit Airlines, Sun Country Airlines, Swiss, TAP Air Portugal, Turkish Airlines, United Airlines, UPS, Virgin Atlantic, WestJet.

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