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Flights from Chicago to Boston

Find cheap airlines flights from Chicago to Boston

Choose from 1 carriers that fly from Chicago to Boston, including Delta Air Lines, Enjoy the cheapest tickets on this route with American Airlines.
Delta Air Lines logo Delta Air Lines

Cheap flight deals from Chicago to Boston

Non stop flight deals! Book direct flights from Chicago to Boston: One way flights from AED 171, round trip flights from AED 303. Cheapest next 3 months.

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

Flight Info | Chicago to Boston

The distance between Chicago and Boston is about 1,371.27 km. It takes around 2 hours 28 minutes on average to fly from Chicago to Boston. The most popular month to Boston is June. The off-season for travel is April.

Cheapest one-way flight price AED 171
Cheapest return ticket price AED 303
Off-season for travel April
Peak season for travel June
Flight distance 1,371.27 km
Average flight time 2 hours 28 minutes
Popular airline Delta Air Lines

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

The cheapest time for Chicago to Boston flights: Sep 7 to Sep 14 — one way flight prices from AED 170.

Cheapest flights
From price
Search
  • 13 20
  • 20 27

  • Aug

    27 3
  • 3 10
  • 10 17
  • 17 24
  • 24 31

  • Sep

    31 7
  • 7 14
  • 14 21
  • 21 28

  • Oct

    28 5
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

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 Thu, Sep 11 at AED 171 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 Jetblue Airways.
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.

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