Good to know - Cheap tickets Boston — Chicago
| Minimal flight time | 2h 45m |
|---|---|
| Flight distance | 1366 km |
| Most popular airline | Southwest Airlines |
| Round-trip from | $41 |
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 | |
|---|---|---|---|---|---|---|---|
| 05:00 | 06:55 | thu, fri, sun | WN699 | Southwest Airlines | 2h 55m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:15 | 07:00 | sat | WN699 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:20 | 07:10 | mon | WN699 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:30 | 07:20 | tue, wed | WN699 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 06:00 | 08:00 | daily | UA1414 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:30 | 08:41 | tue, wed | AA1328 | American Eagle | 3h 11m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:30 | 08:20 | sat | WN833 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 06:52 | 09:03 | mon, thu, fri, sat, sun | AA1328 | American Eagle | 3h 11m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:00 | 09:10 | mon, tue, wed, fri, sat, sun | B6311 | JetBlue | 3h 10m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:05 | 09:00 | sun | WN833 | Southwest Airlines | 2h 55m | Logan International Airport — Chicago Midway International Airport | Select dates |
Popular airlines flying Boston — Chicago
Flight Boston – Chicago is served by 42 airlines. 5 airlines operate direct flights.
Airlines with direct flights
Other airlines flying with transfers
Dynamics airfare Boston — Chicago by month for the last year
according to LowCost.Club for the last year
The airfare depends on the departure date. Our chart shows the low season prices on route Boston — Chicago
The graph shows that booking flights Boston — Chicago is best planned for January and flights Boston — Chicago — Boston in the month of February.
Flights Boston — Chicago
The selection of cheap flights Boston — Chicago
The price of the flight Boston — Chicago (United States) — Boston from $41 (round-trip).
The average price of the flight Boston — Chicago (United States) — Boston $126 (round-trip).
- Departure city: Boston
- IATA code of the city of origin: BOS
- Departure airports: Pease Air Force Base, Logan International Airport, Boston City Heliport
- Departure country: United States
- Destination city: Chicago
- IATA code of the destination city: CHI
- Destination airports: Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport
- Destination country: United States
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 45m.
Routes from nearby cities to Chicago
A flight from a neighbouring city can help you save money on plane tickets.
The closest airports to Boston with a flight to Chicago are in Hartford.
Popular International routes from Boston
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
Are there any direct flights Boston — Chicago?
Yes, they do: WN699, UA1414, AA1328, WN833, B6311, DL2570, DL5860, UA2488, AA1022, UA1349, AA4358, AA4413, UA503, WN527, DL5606, AA2489, UA1732, WN3514, B6811, WN701, AA4628, DL2646, UA2040, AA1245, WN1266, UA1015, AA3901, AA1385, DL5858
Can we fly from Boston to Chicago?
Yes, you can fly from Boston to Chicago. Boston has 3 airports (Pease Air Force Base, Logan International Airport, Boston City Heliport) for flights. Southwest Airlines, United Express, American Eagle, JetBlue, Delta Connection 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, Atlas Air, Austrian Airlines, avianca, British Airways, Cape Air, Cathay Pacific, Contour Aviation, Copa Airlines, Emirates, Etihad Airways (Greenliner Livery), FedEx, Frontier (Penny the Owl Livery), Iberia, Icelandair, Japan Airlines, Jet Linx Aviation, Kalitta Charters, KLM, Korean Air, Lufthansa, NetJets, Pecotox Air, Porter, Porter Airlines Canada, Qatar Airways, Republic Airways, SAS, SkyWest Charter, Slate Aviation, Spirit Airlines, Sun Country Airlines, Swiss, TAP Air Portugal, Turkish Airlines, UPS, Virgin Atlantic.
How long does it take to fly from Boston to Chicago?
A direct flight lasts an average of 2h 45m, during which time the aircraft covers a distance of 1366 km.
How much do flights Boston — Chicago cost?
The price of flights Boston — Chicago starts from $41.
What days does the plane fly Boston — Chicago?
Planes fly Boston — Chicago 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun
What airports are there in Boston and Chicago?
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.
What flights are currently flying from Boston to Chicago?
The following flights fly between Boston and Chicago: WN699, WN699, WN699, WN699, UA1414, AA1328, WN833, AA1328, B6311, WN833, WN833, DL2570, DL5860, UA2488, DL2570, AA1022, B6311, UA1349, UA1349, AA4358, AA4413, UA503, AA4413, WN527, DL5606, WN527, WN527, AA2489, UA1732, UA1732, UA1732, WN527, WN3514, WN3514, B6811, WN701, WN3514, B6811, AA4628, AA4628, DL2646, UA2040, AA1245, WN701, AA1245, WN1266, UA1015, WN1266, UA1015, UA1015, WN1266, AA3901, WN701, AA1385, DL5858
What month is the cheapest to fly from Boston to Chicago?
High season is considered to be July and the cheapest month is January. Enter your preferred airports (or cities) and dates into the search form above to unlock the latest Boston — Chicago flight deals.
Which airlines direct fly from Boston to Chicago?
The following airlines have direct flights Boston — Chicago: Southwest Airlines, United Express, American Eagle, JetBlue, Delta Connection.
Which airlines fly from Boston to Chicago?
All the following airlines flights Boston — Chicago: Aer Lingus, Aeromexico, Air Canada, Air France, Alaska Airlines, Allegiant Air, American Eagle, Atlas Air, Austrian Airlines, avianca, British Airways, Cape Air, Cathay Pacific, Contour Aviation, Copa Airlines, Delta Connection, Emirates, Etihad Airways (Greenliner Livery), FedEx, Frontier (Penny the Owl Livery), Iberia, Icelandair, Japan Airlines, Jet Linx Aviation, JetBlue, Kalitta Charters, KLM, Korean Air, Lufthansa, NetJets, Pecotox Air, Porter, Porter Airlines Canada, Qatar Airways, Republic Airways, SAS, SkyWest Charter, Slate Aviation, Southwest Airlines, Spirit Airlines, Sun Country Airlines, Swiss, TAP Air Portugal, Turkish Airlines, United Express, UPS, Virgin Atlantic.