Flights from Boston to Chicago Starting at NZD 77

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.

Find the best time to fly from Boston to Chicago

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  • 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
  • 8 15
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Airlines Flying from Boston to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Jetblue Airways logo Jetblue Airways American Airlines logo American Airlines Delta Air Lines logo Delta Air Lines United Airlines logo United Airlines Frontier Airlines logo Frontier Airlines

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 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 NZD 399.

  • How long does it take to fly from Boston (BOS) to Chicago (CHI) and what is the distance?

    It takes around 4 hours 14 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 Intl. Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

  • 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.

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
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information from Boston to Chicago

Cheapest one-way flight price NZD 76
Cheapest round-trip ticket price NZD 155
Off-season for travel February
Peak season for travel December
Flight distance 1,371.27 km
Average flight time 4 hours 14 minutes
Popular airline American Airlines

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