Good to know - Cheap tickets Boston — Chicago
| Cheapest flight found | $34 |
|---|---|
| Minimal flight time | 2h 11m |
| Flight distance | 1366 km |
| Most popular airline | American Eagle |
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 |
|---|---|---|
| June 2026 | ||
| May 2026 | ||
| April 2026 | ||
| March 2026 | ||
| January 2026 | ||
| December 2025 | ||
| November 2025 | ||
| October 2025 | ||
| September 2025 | ||
| August 2025 | ||
| July 2025 | ||
| June 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 | 06:58 | mon, tue, wed, thu, fri, sun | AA3324 | American Eagle | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 05:00 | 06:51 | wed, fri | AA3324 | American Eagle | 2h 51m | Logan International Airport — O'Hare International Airport | Select dates |
| 05:15 | 06:50 | thu, sat | WN1431 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:15 | 06:45 | mon, thu, fri | WN2650 | Southwest Airlines | 2h 30m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:28 | 07:24 | daily | AA3324 | American Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 05:30 | 07:05 | sun | WN2650 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:50 | 07:25 | sat | WN2650 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 06:00 | 07:55 | mon, tue, wed, thu, fri, sun | B6311 | JetBlue | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:00 | 07:56 | thu | AA3324 | American Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:10 | 08:08 | sun | DL5719 | Delta Connection | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
Popular airlines flying Boston — Chicago
Flight Boston – Chicago is served by 41 airlines. 7 airlines operate direct flights.
Airlines with direct flights
Other airlines flying with transfers
Sales of tickets from Boston to Chicago in the last 48 hours
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 November and flights Boston — Chicago — Boston in the month of September.
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).
- 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 11m.
LowCostClub always do a comparison of airfares Boston — Chicago with several airlines (include American Eagle, Southwest Airlines, JetBlue). 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 Manchester. 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
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: AA3324, WN1431, WN2650, B6311, DL5719, UA1414, AA1509, DL2570, UA2251, AA1239, 5X2019, WN1435, WN1502, UA600, WN1434, WN1269, UA365, JL15, UA788, UA378, AA1905, AA3048, DL2679, WN1100, AA3287, UA1732, UA3915, AA3672, AA547, AA1457, B6811, AA1859, WN3911, AA2976, AA3711, WN1437, DL5722, DL2646, UA1989, UA1032, AA1913, AA2320, AA1479, UA2040, WN736, WN2190, AA4651, WN1096, AA2837, WN784, WN187, UA1015, AA4778, AA3233, AA4470, DL2676, WN117, UA2229, WN1440, UA3755
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. American Eagle, Southwest Airlines, JetBlue, Delta Connection, United Express, UPS, Jet Linx Aviation depart from Boston on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through ABX Air, Aer Lingus Regional, Aeromexico, Air Canada, Air France, Alaska Airlines, Allegiant Air, Atlas Air, Austrian Airlines, avianca, Breeze Airways, British Airways, Cape Air, Cathay Pacific, Copa Airlines, Emirates, Ethiopian Cargo, Etihad Airways, FedEx, Frontier (Sammy the Squirrel Livery), Iberia, Icelandair, ITA Airways, Japan Airlines, Kalitta Charters, KLM, Korean Air, Lufthansa, NetJets, Porter, Porter Airlines Canada, Qatar Airways, SAS, Slate Aviation, Spirit Airlines, Sun Country Airlines, Swiss, TAP Express, Turkish Airlines, Virgin Atlantic, WestJet.
How long does it take to fly from Boston to Chicago?
A direct flight lasts an average of 2h 11m, 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 $34.
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: AA3324, AA3324, WN1431, WN2650, AA3324, WN2650, WN2650, B6311, AA3324, DL5719, UA1414, B6311, AA1509, B6311, AA1509, AA1509, WN1431, DL2570, DL2570, UA2251, AA1239, AA1239, 5X2019, AA1239, 5X2019, WN1435, WN1502, AA1239, AA1239, WN1435, WN1435, UA600, WN1434, WN1269, UA365, WN1434, JL15, UA788, UA378, AA1905, AA3048, AA1905, DL2679, DL2679, WN1100, AA3287, AA3287, AA3287, UA1732, UA1732, UA3915, UA1732, UA1732, WN1435, AA3672, WN1435, AA547, AA547, UA1732, AA1457, AA547, AA1457, AA1457, AA1457, AA547, AA547, AA547, AA547, B6811, AA1859, B6811, WN3911, AA2976, AA3711, AA3711, AA3048, AA3711, WN1437, WN1435, AA3711, B6811, B6811, AA3711, DL5722, DL2646, DL2646, AA3711, WN2650, UA1989, UA1032, UA1989, AA1913, AA2320, AA1479, AA1479, B6811, DL2646, DL2646, DL2646, UA2040, UA2040, WN736, WN2190, AA4651, WN1096, WN1434, AA2837, WN784, WN187, UA1015, DL2646, UA1015, WN736, WN784, WN1096, AA4778, AA3233, AA4778, AA3233, AA3233, AA3233, AA3233, AA3233, AA4470, AA2837, AA2837, DL2676, WN117, DL2676, DL2676, DL2676, DL2676, UA2229, WN1440, UA2229, UA2229, UA3755
What month is the cheapest to fly from Boston to Chicago?
High season is considered to be July and the cheapest month is November. 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: American Eagle, Southwest Airlines, JetBlue, Delta Connection, United Express, UPS, Jet Linx Aviation.
Which airlines fly from Boston to Chicago?
All the following airlines flights Boston — Chicago: ABX Air, Aer Lingus Regional, Aeromexico, Air Canada, Air France, Alaska Airlines, Allegiant Air, American Eagle, Atlas Air, Austrian Airlines, avianca, Breeze Airways, British Airways, Cape Air, Cathay Pacific, Copa Airlines, Delta Connection, Emirates, Ethiopian Cargo, Etihad Airways, FedEx, Frontier (Sammy the Squirrel Livery), Iberia, Icelandair, ITA Airways, Japan Airlines, Jet Linx Aviation, JetBlue, Kalitta Charters, KLM, Korean Air, Lufthansa, NetJets, Porter, Porter Airlines Canada, Qatar Airways, SAS, Slate Aviation, Southwest Airlines, Spirit Airlines, Sun Country Airlines, Swiss, TAP Express, Turkish Airlines, United Express, UPS, Virgin Atlantic, WestJet.