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Flights from Boston to Chicago
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Flights from Boston to Chicago Starting at Rs 20,670

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

  • One way
  • Round-trip
      • Cheapest nonstop
        BOS07:25
        3h 3m
        Nonstop
        ORD09:28
        Fri, Dec 6|Boston - Chicago|Delta Air Lines
        Rs 20,670Rs 24,215
        15% OFF
        15% OFF
        Rs 24,215Rs 20,670

        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 Fri, Dec 6, arriving at O'Hare International Airport. One-way Prices start from Rs 20,670 including taxes and charges.

      • BOS06:00
        3h 6m
        Nonstop
        ORD08:06
        Fri, Dec 6|Boston - Chicago|Jetblue Airways
        Rs 21,437Rs 24,215
        11% OFF
        11% OFF
        Rs 24,215Rs 21,437

        Choose Jetblue Airways flights from Boston to Chicago. The one-way direct flight with Jetblue Airways departs from General Edward Lawrence Logan International Airport on Fri, Dec 6, arriving at O'Hare International Airport. One-way Prices start from Rs 21,437 including taxes and charges.

      • BOS05:15
        3h 5m
        Nonstop
        ORD07:20
        Fri, Dec 6|Boston - Chicago|American Airlines
        Rs 21,552Rs 24,215
        11% OFF
        11% OFF
        Rs 24,215Rs 21,552

        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 Fri, Dec 6, arriving at O'Hare International Airport. One-way Prices start from Rs 21,552 including taxes and charges.

      • BOS06:00
        8h 57m
        1 stop
        MDW13:57
        Wed, Jan 22|Boston - Chicago|Frontier Airlines
        Rs 11,811
        Rs 11,811

        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 Rs 11,811 including taxes and charges.

      • BOS05:45
        8h 39m
        1 stop
        MDW13:24
        Mon, Jan 6|Boston - Chicago|Frontier Airlines
        Rs 12,195
        Rs 12,195

        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 Mon, Jan 6, arriving at Midway International Airport. One-way Prices start from Rs 12,195 including taxes and charges.

      • BOS06:00
        28h 52m
        1 stop
        ORD09:52
        Thu, Jan 9|Boston - Chicago|Frontier Airlines
        Rs 13,192
        Rs 13,192

        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 Thu, Jan 9, arriving at O'Hare International Airport. One-way Prices start from Rs 13,192 including taxes and charges.

      • BOS05:45
        8h 39m
        1 stop
        MDW13:24
        Wed, Dec 18|Boston - Chicago|Frontier Airlines
        Rs 13,345
        Rs 13,345

        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, Dec 18, arriving at Midway International Airport. One-way Prices start from Rs 13,345 including taxes and charges.

      • BOS08:01
        6h 8m
        1 stop
        MDW13:09
        Tue, Dec 17|Boston - Chicago|Frontier Airlines
        Rs 13,345
        Rs 13,345

        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, Dec 17, arriving at Midway International Airport. One-way Prices start from Rs 13,345 including taxes and charges.

      • BOS06:00
        6h 42m
        1 stop
        MDW11:42
        Tue, Dec 10|Boston - Chicago|Frontier Airlines
        Rs 13,805
        Rs 13,805

        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, Dec 10, arriving at Midway International Airport. One-way Prices start from Rs 13,805 including taxes and charges.

      • BOS06:00
        8h 36m
        1 stop
        ORD13:36
        Tue, Feb 4|Boston - Chicago|Frontier Airlines
        Rs 13,844
        Rs 13,844

        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 Rs 13,844 including taxes and charges.

      • BOS13:00
        3h 5m
        Nonstop
        CHI14:00
        Mon, Dec 2|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

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

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.

Frontier Airlines
From Rs 11,811
Delta Air Lines
From Rs 20,670
Jetblue Airways
From Rs 21,437
American Airlines
From Rs 21,552
Southwest Airlines
From Rs 21,552
United Airlines
From Rs 28,914
Sun Country Airlines
From Rs 39,192
Spirit Airlines
From Rs 41,186
Alaska Airlines
From Rs 71,826

Find more flights and 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 57m
    1 transfer
    MDW
    13:57
    General Edward Lawrence Logan International Airport - Midway International Airport
    Wed, Jan 22Frontier Airlines
    Rs 11,811
  • Frontier Airlines
    BOS
    06:00
    11h 39m
    1 transfer
    ORD
    16:39
    General Edward Lawrence Logan International Airport - O'Hare International Airport
    Wed, Dec 11Frontier Airlines
    Rs 14,496
  • Frontier Airlines
    BOS
    06:00
    11h 39m
    1 transfer
    ORD
    16:39
    General Edward Lawrence Logan International Airport - O'Hare International Airport
    Wed, Dec 11Frontier Airlines
    Rs 14,496
    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 Rs 51,731.

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

    It takes around 2 hours 57 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 priceRs 11,811
Cheapest round-trip ticket priceRs 28,876
Off-season for travelDecember
Peak season for travelFebruary
Flight distance1,371.27 km
Average flight time2 hours 57 minutes
Popular airlineAmerican Airlines

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