Cheap Flights from Boston to Chicago
We've found these cheap flights for you. You can book one-way or round-trip flight tickets.
Swipe up to view more
>
>
>
>
>
Flights from Boston to Chicago
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.
Find cheap flights from Boston to Chicago
We've found these cheap flights for you. You can book one-way or round-trip flight tickets.
-
Round-trip
-
One way
-
-
Cheapest nonstop
BOS 05:502h 40mNonstopMDW 07:30Boston - Chicago | Wed, Jun 4 | Southwest Airlines
MDW 13:252h 20mNonstopBOS 16:45Chicago - Boston | Tue, Jun 10 | Southwest AirlinesUS$85 US$26268% OFF68% OFFUS$262 US$85 -
BOS 05:152h 35mNonstopMDW 06:50Boston - Chicago | Sat, Jul 5 | Southwest Airlines
MDW 05:052h 10mNonstopBOS 08:15Chicago - Boston | Tue, Jul 8 | Southwest AirlinesUS$89 US$26266% OFF66% OFFUS$262 US$89
-
BOS 05:152h 35mNonstopMDW 06:50Boston - Chicago | Sat, Jun 7 | Southwest Airlines
ORD 06:002h 15mNonstopBOS 09:15Chicago - Boston | Mon, Jun 9 | Southwest AirlinesUS$90 US$26266% OFF66% OFFUS$262 US$90
-
BOS 17:202h 50mNonstopMDW 19:10Boston - Chicago | Tue, Jun 17 | Southwest Airlines
MDW 05:052h 10mNonstopBOS 08:15Chicago - Boston | Tue, Jun 24 | Southwest AirlinesUS$9165% OFFUS$262 US$91
-
BOS 19:233h 2mNonstopORD 21:25Boston - Chicago | Wed, Jun 4 | American Airlines
ORD 07:302h 26mNonstopBOS 10:56Chicago - Boston | Tue, Jun 10 | American AirlinesUS$9265% OFFUS$262 US$92 -
BOS 06:583h 1mNonstopORD 08:59Boston - Chicago | Tue, Jun 17 | American Airlines
ORD 06:002h 15mNonstopBOS 09:15Chicago - Boston | Sat, Jun 21 | Southwest AirlinesUS$9265% OFFUS$262 US$92
-
BOS 06:003hNonstopORD 08:00Boston - Chicago | Wed, Jun 4 | Jetblue Airways
MDW 13:252h 20mNonstopBOS 16:45Chicago - Boston | Tue, Jun 10 | Southwest AirlinesUS$9265% OFFUS$262 US$92 -
BOS 06:413hNonstopORD 08:41Boston - Chicago | Sat, Jun 7 | American Airlines
ORD 20:402h 40mNonstopBOS 00:20Chicago - Boston | Mon, Jun 9 | American AirlinesUS$14146% OFFUS$262 US$141
-
BOS 06:583h 1mNonstopORD 08:59Boston - Chicago | Wed, Jun 18 | American Airlines
ORD 20:402h 46mNonstopBOS 00:26Chicago - Boston | Sat, Jun 21 | American AirlinesUS$20522% OFFUS$262 US$205
-
BOS 06:002h 55mNonstopORD 07:55Boston - Chicago | Wed, Jun 18 | Jetblue Airways
ORD 20:402h 46mNonstopBOS 00:26Chicago - Boston | Sat, Jun 21 | American AirlinesUS$20721% OFFUS$262 US$207
-
BOS 13:0017h 25m1 stopsCHI Invalid DateBoston - Chicago | Thu, May 22 | Normal Airline
CHI 15:006hNonstopBOS 16:00Chicago - Boston | Sat, May 24 | Normal AirlineFind More FlightsFind More Flights
-
Cheapest nonstop
BOS 05:152h 35mNonstopMDW 06:50Boston - Chicago | Sat, Jul 5 | Southwest AirlinesUS$44 US$29185% OFF85% OFFUS$291 US$44
-
BOS 05:502h 40mNonstopMDW 07:30Boston - Chicago | Wed, May 28 | Southwest AirlinesUS$44 US$29185% OFF85% OFFUS$291 US$44
-
BOS 17:202h 50mNonstopMDW 19:10Boston - Chicago | Tue, Jun 17 | Southwest AirlinesUS$44 US$29185% OFF85% OFFUS$291 US$44
-
BOS 05:252h 35mNonstopMDW 07:00Boston - Chicago | Wed, Jun 18 | Southwest AirlinesUS$4585% OFFUS$291 US$45
-
BOS 05:152h 35mNonstopMDW 06:50Boston - Chicago | Sat, Jun 7 | Southwest AirlinesUS$4784% OFFUS$291 US$47
-
BOS 05:152h 35mNonstopMDW 06:50Boston - Chicago | Sat, Jun 14 | Southwest AirlinesUS$5282% OFFUS$291 US$52
-
BOS 17:382h 58mNonstopORD 19:36Boston - Chicago | Wed, May 28 | American AirlinesUS$10464% OFFUS$291 US$104
-
BOS 14:082h 55mNonstopORD 16:03Boston - Chicago | Tue, Jun 17 | American AirlinesUS$10464% OFFUS$291 US$104
-
BOS 07:152h 54mNonstopORD 09:09Boston - Chicago | Sun, May 25 | Delta Air LinesUS$20430% OFFUS$291 US$204 -
BOS 07:152h 54mNonstopORD 09:09Boston - Chicago | Wed, May 21 | Delta Air LinesUS$23021% OFFUS$291 US$230
-
BOS 13:0017h 25m1 stopsCHI Invalid DateBoston - Chicago | Thu, May 22 | Normal AirlineFind More FlightsFind More Flights
-
Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
Boston to Chicago Flight Information
| Cheapest one-way flight price | $43 |
|---|---|
| Cheapest round-trip ticket price | $84 |
| Off-season for travel | April |
| Peak season for travel | February |
| Flight distance | 1,371.27 km |
| Average flight time | 2 hours 56 minutes |
| Popular airline | American Airlines |
When is the cheapest time to book flights from Boston to Chicago?
We monitor flight fares to help you find the best deals effortlessly
Cheapest flights
From price
Search
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Frequently Asked Questions
-
When are flight tickets from Boston (BOS) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Boston to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that 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 $230. -
How long does it take to fly from Boston (BOS) to Chicago (CHI) and what is the distance?
It takes around 2 hours 56 minutes to fly from Boston (BOS) to Chicago (CHI). -
What are the most popular airlines that fly from Boston (BOS) to Chicago (CHI)?
Airlines with flights from Boston (BOS) to Chicago (CHI): Alaska Airlines, El Al, United Airlines, KLM, American Airlines, Royal Jordanian, Icelandair, Korean Air, Southwest Airlines, Jetblue Airways, LATAM Airlines and Qatar Airways.
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, Jul 5 at US$44 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 Southwest 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 Boston to Chicago 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 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 free app and search for cheap flight tickets from Boston to Chicago to get exclusive deals for you.
More Travel Options
-
Top Routes from Boston
-
Top Routes to Chicago
-
Popular Airlines
- Direct flights from Boston to Chicago
- Cheap flights from Boston to Washington D.C.
- Direct flights from Boston to New York
- Cheap flights from Boston to Toronto
- Cheap flights from Boston to Phnom Penh
- Cheap flights from Boston to Miami
- Cheap flights from Boston to Paris
- Return flights from Boston to Los Angeles
- Direct flights from Boston to Montreal
- Direct flights from Boston to San Francisco
- Cheap flights from Hong Kong to Chicago
- Cheap flights from Los Angeles to Chicago
- Cheap flights from San Francisco to Chicago
- Direct flights from Mexico City to Chicago
- Direct flights from Amman to Chicago
- Direct flights from New York to Chicago
- Cheap flights from Shanghai to Chicago
- Return flights from Tokyo to Chicago
- Direct flights from Seoul to Chicago
- Direct flights from Seattle to Chicago