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Flights from Boston to Chicago
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Find cheap one-way flights from Boston to Chicago starting at US$38.
Book one-way or return flights from Boston to Chicago from as little as US$38. Choose from the popular airlines below and book your flight today!
- One way
- Round-trip
- BOS08:219h 40m1 stopMDW17:01Wed, Mar 20|Boston - Chicago|Frontier AirlinesUS$38US$8354% OFF54% OFFUS$83US$38
- BOS11:536h 8m1 stopMDW17:01Tue, Apr 9|Boston - Chicago|Frontier AirlinesUS$47US$8343% OFF43% OFFUS$83US$47
- BOS21:502h 45mDirectMDW23:35Thu, Mar 21|Boston - Chicago|Southwest AirlinesUS$48US$8342% OFF42% OFFUS$83US$48
- BOS12:4611h 44m1 stopMDW23:30Wed, May 1|Boston - Chicago|Frontier AirlinesUS$48US$48
- BOS12:4611h 37m1 stopMDW23:23Wed, Apr 10|Boston - Chicago|Frontier AirlinesUS$48US$48
- BOS06:552h 40mDirectMDW08:35Wed, Mar 20|Boston - Chicago|Southwest AirlinesUS$50US$50
- BOS12:4611h 44m1 stopMDW23:30Wed, May 8|Boston - Chicago|Frontier AirlinesUS$54US$54
- BOS06:302h 45mDirectMDW08:15Mon, Mar 25|Boston - Chicago|Southwest AirlinesUS$57US$57
- BOS09:4526h 9m1 stopMDW10:54Wed, Apr 3|Boston - Chicago|Frontier AirlinesUS$57US$57
- BOS12:4111h1 stopMDW22:41Sat, Apr 20|Boston - Chicago|Frontier AirlinesUS$59US$59
- BOS13:003h 5mDirectCHI14:00Tue, Mar 26|Boston - Chicago|Frontier AirlinesFind More FlightsFind More Flights
Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
When is the cheapest time to book flights from Boston to Chicago?
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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Cheapest airlines flights from Boston to Chicago
Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Frontier Airlines
From US$38
Southwest Airlines
From US$48
Jetblue Airways
From US$69
Spirit Airlines
From US$82
Sun Country Airlines
From US$128
Delta Air Lines
From US$138
Alaska Airlines
From US$180
Allegiant Air
From US$208
United Airlines
From US$209
American Airlines
From US$263
ANA airlines
Find more flights and airlines
Find cheap flights from Boston to Chicago by different airports
Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Boston to Chicago.
- CheapestBOS08:219h 40m1 transferMDW17:01General Edward Lawrence Logan International Airport - Midway International AirportWed, Mar 20Frontier AirlinesUS$38
- BOS06:552h 59mDirectORD08:54General Edward Lawrence Logan International Airport - O'Hare International AirportThu, Mar 21American AirlinesUS$263
- BNH09:2012h 27m1 transferORD20:47Hartford Barnes Airport - O'Hare International AirportSat, Apr 13Southern Airways ExpressUS$510
- BNH09:2012h 27m1 transferORD20:47Hartford Barnes Airport - O'Hare International AirportSat, Apr 13Southern Airways ExpressUS$510Find More Flights
Frequently Asked Questions
Boston to Chicago Flight Information
Cheapest nonstop flight price | $38 |
---|---|
Cheapest round-trip ticket price | $102 |
Off-season for travel | December |
Peak season for travel | June |
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