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Flights from Chicago to Boston
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Find cheap one-way flights from Chicago to Boston starting at US$50.
We've found these cheap flights for you. You can book one-way or round-trip flight tickets.
- One way
- Round-trip
- ORD20:152h 32mDirectBOS23:47Wed, Apr 24|Chicago - Boston|Delta Air LinesUS$50US$7130% OFF30% OFFUS$71US$50
- ORD08:212h 23mDirectBOS11:44Wed, May 8|Chicago - Boston|American AirlinesUS$50US$7130% OFF30% OFFUS$71US$50
- MDW20:052h 10mDirectBOS23:15Sat, Mar 30|Chicago - Boston|Southwest AirlinesUS$51US$7128% OFF28% OFFUS$71US$51
- ORD20:102h 36mDirectBOS23:46Wed, May 8|Chicago - Boston|Delta Air LinesUS$51US$51
- ORD17:4613h 18m1 stopBOS08:04Sun, May 5|Chicago - Boston|Spirit AirlinesUS$52US$52
- MDW20:1710h 51m1 stopBOS08:08Sat, Apr 13|Chicago - Boston|Frontier AirlinesUS$57US$57
- ORD18:2113h 24m1 stopBOS08:45Thu, Apr 4|Chicago - Boston|Frontier AirlinesUS$57US$57
- MDW19:3412h 11m1 stopBOS08:45Tue, Apr 2|Chicago - Boston|Frontier AirlinesUS$60US$60
- MDW18:0812h 13m1 stopBOS07:21Mon, Apr 29|Chicago - Boston|Frontier AirlinesUS$60US$60
- ORD08:2522h 43m1 stopBOS08:08Mon, May 13|Chicago - Boston|Frontier AirlinesUS$60US$60
- CHI13:003h 5mDirectBOS14:00Fri, Apr 5|Chicago - Boston|Delta Air LinesFind More FlightsFind More Flights
Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
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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 Chicago to Boston
Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Delta Air Lines
From US$50
Southwest Airlines
From US$51
Frontier Airlines
From US$57
American Airlines
From US$79
Spirit Airlines
From US$82
Jetblue Airways
From US$86
Sun Country Airlines
From US$128
Alaska Airlines
From US$184
United Airlines
From US$214
ANA airlines
Find more flights and airlines
Find cheap flights from Chicago to Boston by different airports
Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Chicago to Boston.
- CheapestMDW20:052h 10mDirectBOS23:15Midway International Airport - General Edward Lawrence Logan International AirportSat, Mar 30Southwest AirlinesUS$51
- ORD08:219h 12m1 transferBOS18:33O'Hare International Airport - General Edward Lawrence Logan International AirportTue, May 14Spirit AirlinesUS$82
- ORD08:219h 12m1 transferBOS18:33O'Hare International Airport - General Edward Lawrence Logan International AirportTue, May 14Spirit AirlinesUS$82Find More Flights
Frequently Asked Questions
Chicago to Boston Flight Information
Cheapest nonstop flight price | $49 |
---|---|
Cheapest round-trip ticket price | $95 |
Off-season for travel | November |
Peak season for travel | September |
Plan Your Trip Around Boston
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