Flight deals from Boston to Chicago

We've found these cheap flights for you. You can book one-way or return flight tickets.

Round-trip
One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Flight Information from Boston to Chicago

Cheapest one-way flight price	£34
Cheapest return ticket price	£65
Off-season travel month	February
Peak season for travel	January
Flight distance	1,371.27km
Average flight time	2 hours 58 minutes
Popular airline	United Airlines

Find the best time to fly from Boston to Chicago

We monitor flight fares to help you find the best deals effortlessly

Cheapest flights

From price

20 27
May

27 4
4 11
11 18
18 25
Jun

25 1
1 8
8 15
15 22
22 29
Jul

29 6
6 13

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

FAQ

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 cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Boston (BOS) to Chicago (CHI) cost?

According to Trip.com's data, the lowest price is around £171.
How long is the flight from Boston (BOS) to Chicago (CHI)?

It takes about 2 hours 58 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): El Al, United Airlines, KLM, Icelandair, Korean Air, American Airlines, Southwest Airlines, Jetblue Airways, Etihad Airways, Qatar Airways, Scandinavian Airlines, Iberia, WestJet and LATAM Airlines.
How many airports in Chicago (CHI)?

There are 3 airport(s) in 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.

Be flexible with your travel dates to get the cheapest flight from Boston to Chicago.

Simply tap "Date" on the flight search bar to browse through the calendar and check out airfare from Boston to Chicago over the next 6 months in 2025. If you're planning to fly within the next three months, it looks like the most affordable option is on Wed, Jun 4, with one-way flights priced at just £35.

Compare cheap flight deals from Boston to Chicago across hundreds of airlines.

With our extensive search, you can compare prices from over 500 airlines to find the cheapest flight tickets from Boston to Chicago. The cheapest airline for this route is Delta Air Lines.

Set up a Price Alert

By setting up a Price Alert for your journey from Boston to Chicago, you can easily keep an eye on ticket prices without having to check every day.

Don't miss out on cheap flight deals and promo codes from Boston to Chicago.

You can always find the latest offers through Trip.com Deals and Promo Codes for cheap flights. By signing up for a free membership, you'll get access to even more deals for your flights.

Book early or wait until the last minute.

It's usually best to book early. Flight tickets are often cheapest when they're first released, typically about a year before the departure date. So, have a look online as soon as the flights you're interested in become available. If you miss the cheapest time, you might still find some good deals as the departure date gets closer.

Search for flights on the go.

For the best travel flight booking experience, download the Trip.com app. You can search for cheap flights from Boston to Chicago and snag some exclusive deals just for you.