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Flights from Boston to Chicago
Cheap flight deals from Boston to Chicago Starting at AED 176
We've found these cheap flights for you. You can book one-way or round-trip flight tickets.
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Round-trip
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One way
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Cheapest nonstopBOS 19:073h 7mNonstopORD 21:14Boston - Chicago | Tue, Apr 29 | American AirlinesORD 07:052h 30mNonstopBOS 10:35Chicago - Boston | Wed, Apr 30 | American AirlinesAED 485 AED 96750% OFF50% OFFAED 967 AED 485
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BOS 07:253h 2mNonstopORD 09:27Boston - Chicago | Tue, Apr 8 | Delta Air LinesORD 18:552h 31mNonstopBOS 22:26Chicago - Boston | Tue, Apr 8 | Delta Air LinesAED 500 AED 96748% OFF48% OFFAED 967 AED 500
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BOS 06:008h 59m1 stopsMDW 13:59Boston - Chicago | Wed, Mar 19 | Frontier AirlinesORD 14:279h 4m1 stopsBOS 00:31Chicago - Boston | Wed, Mar 26 | Frontier AirlinesAED 332 AED 96766% OFF66% OFFAED 967 AED 332
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BOS 05:107h 24m1 stopsMDW 11:34Boston - Chicago | Mon, Mar 24 | Frontier AirlinesORD 11:0012h 25m1 stopsBOS 00:25Chicago - Boston | Wed, Mar 26 | Frontier AirlinesAED 35164% OFFAED 967 AED 351
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BOS 06:0027h 49m1 stopsORD 08:49Boston - Chicago | Thu, Apr 3 | Frontier AirlinesMDW 05:1527h 20m1 stopsBOS 09:35Chicago - Boston | Thu, Apr 10 | Frontier AirlinesAED 37062% OFFAED 967 AED 370
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BOS 06:0027h 55m1 stopsORD 08:55Boston - Chicago | Thu, Mar 20 | Frontier AirlinesORD 12:0211h 29m1 stopsBOS 00:31Chicago - Boston | Tue, Mar 25 | Frontier AirlinesAED 37761% OFFAED 967 AED 377
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BOS 12:4811h 59m1 stopsMDW 23:47Boston - Chicago | Mon, May 5 | Frontier AirlinesORD 16:157h 31m1 stopsBOS 00:46Chicago - Boston | Sat, May 10 | Frontier AirlinesAED 39259% OFFAED 967 AED 392
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BOS 06:0012h 26m1 stopsORD 17:26Boston - Chicago | Wed, Mar 26 | Frontier AirlinesMDW 15:008h 30m1 stopsBOS 00:30Chicago - Boston | Wed, Apr 2 | Frontier AirlinesAED 39259% OFFAED 967 AED 392
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BOS 06:0028h 5m1 stopsORD 09:05Boston - Chicago | Tue, Mar 18 | Frontier AirlinesMDW 15:148h 17m1 stopsBOS 00:31Chicago - Boston | Wed, Mar 26 | Frontier AirlinesAED 39559% OFFAED 967 AED 395
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BOS 11:5812h 34m1 stopsORD 23:32Boston - Chicago | Sat, May 10 | Frontier AirlinesORD 16:157h 29m1 stopsBOS 00:44Chicago - Boston | Mon, May 12 | Frontier AirlinesAED 39859% OFFAED 967 AED 398
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BOS 06:0018h 32m1 stopsORD 23:32Boston - Chicago | Tue, May 6 | Frontier AirlinesORD 16:157h 31m1 stopsBOS 00:46Chicago - Boston | Sat, May 10 | Frontier AirlinesAED 40159% OFFAED 967 AED 401
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BOS 09:1214h 28m1 stopsMDW 22:40Boston - Chicago | Sat, Mar 22 | Frontier AirlinesMDW 16:407h 4m1 stopsBOS 00:44Chicago - Boston | Sat, Mar 29 | Frontier AirlinesAED 8809% OFFAED 967 AED 880
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BOS 13:0017h 25m1 stopsCHI Invalid DateBoston - Chicago | Tue, Mar 18 | Normal AirlineCHI 15:006hNonstopBOS 16:00Chicago - Boston | Thu, Mar 20 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstopBOS 19:123h 4mNonstopORD 21:16Boston - Chicago | Sat, Apr 26 | American AirlinesAED 231 AED 55959% OFF59% OFFAED 559 AED 231
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BOS 07:053hNonstopORD 09:05Boston - Chicago | Wed, Apr 16 | Jetblue AirwaysAED 231 AED 55959% OFF59% OFFAED 559 AED 231
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BOS 06:008h 59m1 stopsMDW 13:59Boston - Chicago | Wed, Mar 26 | Frontier AirlinesAED 176 AED 55969% OFF69% OFFAED 559 AED 176
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BOS 06:008h 59m1 stopsMDW 13:59Boston - Chicago | Wed, Mar 19 | Frontier AirlinesAED 17968% OFFAED 559 AED 179
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BOS 05:107h 24m1 stopsMDW 11:34Boston - Chicago | Mon, Mar 24 | Frontier AirlinesAED 18567% OFFAED 559 AED 185
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BOS 12:4811h 23m1 stopsORD 23:11Boston - Chicago | Mon, Apr 28 | Frontier AirlinesAED 18767% OFFAED 559 AED 187
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BOS 05:107h 24m1 stopsMDW 11:34Boston - Chicago | Mon, Mar 17 | Frontier AirlinesAED 19365% OFFAED 559 AED 193
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BOS 06:0027h 55m1 stopsORD 08:55Boston - Chicago | Thu, Mar 20 | Frontier AirlinesAED 20563% OFFAED 559 AED 205
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BOS 06:007h 18m1 stopsORD 12:18Boston - Chicago | Wed, Apr 9 | Frontier AirlinesAED 20563% OFFAED 559 AED 205
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BOS 06:007h 24m1 stopsMDW 12:24Boston - Chicago | Fri, May 2 | Frontier AirlinesAED 20763% OFFAED 559 AED 207
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BOS 06:007h 31m1 stopsMDW 12:31Boston - Chicago | Thu, Apr 24 | Frontier AirlinesAED 20863% OFFAED 559 AED 208
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BOS 05:0117h 55m1 stopsMDW 21:56Boston - Chicago | Sat, Mar 22 | Frontier AirlinesAED 5089% OFFAED 559 AED 508
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BOS 13:0017h 25m1 stopsCHI Invalid DateBoston - Chicago | Tue, Mar 18 | Normal AirlineFind More FlightsFind More Flights
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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.
Frequently Asked Questions
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When are flight tickets from Boston (BOS) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Boston to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays. -
How much do flights from Boston (BOS) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around AED 842. -
How long does it take to fly from Boston (BOS) to Chicago (CHI)?
It takes about 4 hours 17 minutes to fly from Boston (BOS) to Chicago (CHI). -
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25 km, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14 km, by taxi about 30 minutes.
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What time does the earliest flight from Boston to Chicago depart?
The earliest flight departs from Boston (BOS) at 05:14 and arrives in Chicago (ORD) at 07:15. -
What time does the latest flight from Boston to Chicago depart?
The latest flight departs from Boston (BOS) at 20:20 and arrives in Chicago (ORD) at 22:19. -
What are the most popular airlines that fly from Boston (BOS) to Chicago (CHI)?
Airlines with flights from Boston (BOS) to Chicago (CHI): United Airlines, Southwest Airlines, El Al, Alaska Airlines, Qatar Airways, Icelandair, Korean Air and Jetblue Airways. -
What's the most popular airline for non-stop flights from Boston (BOS) to Chicago (CHI)?
Delta Air Lines operates 10 non-stop flights from Boston (BOS) to Chicago (CHI). -
How many airports are there in Chicago (CHI)?
There are 3 airport(s) near Chicago (CHI): Midway International Airport, O'Hare International Airport and Chicago Rockford International Airport.
How to find a cheap flight from Boston to Chicago
Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Boston to Chicago. Book your flights at the right time and save more.
Being flexible with your dates to get the cheapest Boston to Chicago ticket.
Tap "Date" on flight search bar to scan through the calender for Boston to Chicago airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Sat, Apr 26 at AED 231 for one-way flights.
Compare cheap Boston to Chicago flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Boston to Chicago. The cheapest airline operating is American Airlines.
Set up a Price Alert
By setting up a Price Alert for your Boston to Chicago route, you can easily track the price of your airline tickets from without manually checking every day.
Don't miss cheap Boston to Chicago flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Boston to Chicago to get exclusive deals for you.
Flight Info | Boston to Chicago
Cheapest direct flight price | AED 175 |
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Cheapest return ticket price | AED 438 |
Off-season for travel | February |
Peak season for travel | December |
Flight distance | 1,371.27 km |
Average flight time | 4 hours 17 minutes |
Popular airline | Jetblue Airways |
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