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Flights from Boston to Chicago
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Flights from Boston to Chicago Starting at €37

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

  • One way
  • Round-trip
      • Cheapest nonstop
        BOS11:00
        3h 8m
        Nonstop
        ORD13:08
        Thu, Jan 16|Boston - Chicago|Delta Air Lines
        €76€141
        46% OFF
        46% OFF
        €141€76

        Choose Delta Air Lines flights from Boston to Chicago. The one-way direct flight with Delta Air Lines departs from General Edward Lawrence Logan International Airport on Thu, Jan 16, arriving at O'Hare International Airport. One-way Prices start from €76 including taxes and charges.

      • BOS08:45
        3h
        Nonstop
        ORD10:45
        Thu, Jan 16|Boston - Chicago|American Airlines
        €101€141
        28% OFF
        28% OFF
        €141€101

        Choose American Airlines flights from Boston to Chicago. The one-way direct flight with American Airlines departs from General Edward Lawrence Logan International Airport on Thu, Jan 16, arriving at O'Hare International Airport. One-way Prices start from €101 including taxes and charges.

      • BOS06:00
        8h 34m
        1 stop
        ORD13:34
        Tue, Jan 14|Boston - Chicago|Frontier Airlines
        €37€141
        74% OFF
        74% OFF
        €141€37

        Choose Frontier Airlines flights from Boston to Chicago. The one-way connecting flight with Frontier Airlines departs from General Edward Lawrence Logan International Airport on Tue, Jan 14, arriving at O'Hare International Airport. One-way Prices start from €37 including taxes and charges.

      • BOS06:00
        8h 57m
        1 stop
        MDW13:57
        Wed, Jan 22|Boston - Chicago|Frontier Airlines
        €41
        €41

        Choose Frontier Airlines flights from Boston to Chicago. The one-way connecting flight with Frontier Airlines departs from General Edward Lawrence Logan International Airport on Wed, Jan 22, arriving at Midway International Airport. One-way Prices start from €41 including taxes and charges.

      • BOS06:00
        11h 16m
        1 stop
        MDW16:16
        Tue, Feb 11|Boston - Chicago|Frontier Airlines
        €44
        €44

        Choose Frontier Airlines flights from Boston to Chicago. The one-way connecting flight with Frontier Airlines departs from General Edward Lawrence Logan International Airport on Tue, Feb 11, arriving at Midway International Airport. One-way Prices start from €44 including taxes and charges.

      • BOS06:00
        9h 25m
        1 stop
        ORD14:25
        Wed, Feb 12|Boston - Chicago|Frontier Airlines
        €45
        €45

        Choose Frontier Airlines flights from Boston to Chicago. The one-way connecting flight with Frontier Airlines departs from General Edward Lawrence Logan International Airport on Wed, Feb 12, arriving at O'Hare International Airport. One-way Prices start from €45 including taxes and charges.

      • BOS06:00
        8h 36m
        1 stop
        ORD13:36
        Tue, Feb 4|Boston - Chicago|Frontier Airlines
        €46
        €46

        Choose Frontier Airlines flights from Boston to Chicago. The one-way connecting flight with Frontier Airlines departs from General Edward Lawrence Logan International Airport on Tue, Feb 4, arriving at O'Hare International Airport. One-way Prices start from €46 including taxes and charges.

      • BOS06:00
        11h 16m
        1 stop
        MDW16:16
        Tue, Jan 28|Boston - Chicago|Frontier Airlines
        €48
        €48

        Choose Frontier Airlines flights from Boston to Chicago. The one-way connecting flight with Frontier Airlines departs from General Edward Lawrence Logan International Airport on Tue, Jan 28, arriving at Midway International Airport. One-way Prices start from €48 including taxes and charges.

      • BOS06:00
        14h 6m
        1 stop
        MDW19:06
        Wed, Jan 29|Boston - Chicago|Frontier Airlines
        €48
        €48

        Choose Frontier Airlines flights from Boston to Chicago. The one-way connecting flight with Frontier Airlines departs from General Edward Lawrence Logan International Airport on Wed, Jan 29, arriving at Midway International Airport. One-way Prices start from €48 including taxes and charges.

      • BOS06:00
        7h 45m
        1 stop
        ORD12:45
        Wed, Feb 5|Boston - Chicago|Frontier Airlines
        €49
        €49

        Choose Frontier Airlines flights from Boston to Chicago. The one-way connecting flight with Frontier Airlines departs from General Edward Lawrence Logan International Airport on Wed, Feb 5, arriving at O'Hare International Airport. One-way Prices start from €49 including taxes and charges.

      • BOS01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Tue, Jan 21|Boston - Chicago|Delta Air Lines
        Find More Flights
        Find More Flights

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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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 logoJetblue AirwaysDelta Air Lines logoDelta Air LinesAmerican Airlines logoAmerican AirlinesUnited Airlines logoUnited AirlinesSpirit Airlines logoSpirit Airlines

Alternative Routes from Boston to Chicago

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Boston to Chicago.

  • Cheapest
    Frontier Airlines
    BOS
    06:00
    8h 34m
    1 transfer
    ORD
    13:34
    General Edward Lawrence Logan International Airport - O'Hare International Airport
    Tue, Jan 14Frontier Airlines
    €37
  • Frontier Airlines
    BOS
    06:00
    11h 14m
    1 transfer
    MDW
    16:14
    General Edward Lawrence Logan International Airport - Midway International Airport
    Tue, Jan 14Frontier Airlines
    €37
  • Frontier Airlines
    BOS
    06:00
    11h 14m
    1 transfer
    MDW
    16:14
    General Edward Lawrence Logan International Airport - Midway International Airport
    Tue, Jan 14Frontier Airlines
    €37
    Find More Flights

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 €179.

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

    It takes around 3 hours 21 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. 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)?

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 nonstop flight price€36
Cheapest round-trip ticket price€103
Off-season for travelDecember
Peak season for travelApril
Flight distance1,371.27 km
Average flight time3 hours 21 minutes
Popular airlineAmerican Airlines

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