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Compare Cheap Flights from Boston to Chicago

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Round Trip Flights from Boston to Chicago

13 Sep
BOS
21 Sep
ORD
$ 136.96
13 Sep
BOS
21 Sep
ORD
$ 139.96
13 Sep
BOS
21 Sep
ORD
$ 174.96
07 Aug
BOS
10 Aug
MDW
$ 219.98
17 Oct
BOS
19 Oct
ORD
$ 228.77
16 Oct
BOS
20 Oct
ORD
$ 321.76
*Note: All fares are quoted in USD.

Last updated on Wednesday 07/30/2025 at 05:00 AM, the fares mentioned above are for flight tickets and inclusive of fuel surcharges, service fee and taxes. Based on historical data, these fares are subject to change without prior notice and cannot be guaranteed at the time of booking. Kindly go through our terms and conditions before booking.

Book Boston To Chicago Flights

Known as The Windy City, Chicago and dominated by skyscrapers, the city is perched beautifully along the shores of Lake Michigan with its lively cultural hues. When it comes to exploring the urban suburbs, many tourist attractions in Chicago are lined across the 77 neighborhoods. Only a few of us know that Chicago is divided into 77 communities where you can eat, shop, and explore. Places like Grant Park and Buckingham Fountain, Riverwalk Chicago, and the Art Institute of Chicago are among the top attractions you can visit.

Why plan a vacation in Chicago? There can be multiple reasons like world class attractions, fun activities, wide variety of food that tastes amazing, and festivals drawing thousands of people. You can ride the Navy Pier, a 196-foot Ferris wheel with an observation deck, to capture the stunning beauty of the city. You can also plan a day out to North Avenue Beach and enjoy a swim or go paddleboarding and wakeboarding. The city also hosts varuous events and festivals from June to August, which is why flights from Boston to Chicago are mostly expensive. Shoulder season in Chicago falls between June (the spring season) and October, and Boston to Chicago flights are usually cheaper. Book flights to O'Hare International Airport and Midway International Airport, serving as the international gateway for the city. Spirit, JetBlue Delta, and Southwest Airlines are a few US carriers that operate regular BOS to CHI flights from Boston Logan International Airport.

To get cheaper Chicago flights from Boston, call our executives. Our team is available 24/7 to assist you with cheap flight bookings.

Finding Cheap Flights From Boston To Chicago : Frequently Asked Questions

* The mentioned flight facts are based on the last 3 months' data. Information regarding the highest and lowest booking months is based on the last 12 months' data.

Major Carriers Operating Flights From Boston To Chicago
Airline Cheapest Average

UNITED AIRLINES $101 $232

AMERICAN AIRLINES $68 $205

ALASKA AIRLINES $66 $208

Low Cost Carriers Operating Flights From Boston To Chicago
Airline Cheapest Average

ALASKA AIRLINES $66 $208

AMERICAN AIRLINES $68 $205

SPIRIT AIRLINES $69 $214

Inspiration to Escape the Mundane

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