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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  • 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 Boston to Chicago?

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

Cheapest flights
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  • 16 23
  • 23 30

  • Apr

    30 6
  • 6 13
  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
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 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.

  • 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)?

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.
1
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.
2
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.
3
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.
4
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.
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 Boston to Chicago to get exclusive deals for you.

Flight Info | Boston to Chicago

Cheapest direct flight price AED 175
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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