Trip.com
>
Flights
>
Flights to United States
>
Flights to Massachusetts
>
Flights to Boston
>
Flights from Chicago to Boston

Cheap flight deals from Chicago to Boston

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

  • Round-trip
  • One way

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

When is the cheapest time to fly from Chicago to Boston?

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

Cheapest flights
From price
Search
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
  • 8 15
  • 15 22
  • 22 29

  • Jul

    29 6
  • 6 13
  • 13 20
  • 20 27
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Find cheap 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 logo Delta Air Lines

Frequently Asked Questions

How to find a cheap flight from Chicago to Boston

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 Chicago to Boston. Book your flights at the right time and save more.
1
Being flexible with your dates to get the cheapest Chicago to Boston ticket.
Tap "Date" on flight search bar to scan through the calender for Chicago to Boston 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, Jun 21 at AED 163 for one-way flights.
2
Compare cheap Chicago to Boston 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 Chicago to Boston. The cheapest airline operating is Southwest Airlines.
3
Set up a Price Alert
By setting up a Price Alert for your Chicago to Boston route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Chicago to Boston 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.
5
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.
6
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 Chicago to Boston to get exclusive deals for you.

Flight Info | Chicago to Boston

Cheapest one-way flight price AED 137
Cheapest return ticket price AED 302
Off-season for travel March
Peak season for travel June
Flight distance 1,371.27 km
Average flight time 2 hours 26 minutes
Popular airline American Airlines

More Travel Options

  • Top Routes from Chicago
  • Top Routes to Boston
  • Trending Airlines