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Latest Flight Deals from Boston to Chicago

Book one-way or return flights from Boston to Chicago from as little as NZD 60. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip
      • BOS06:30
        2h 54m
        Direct
        ORD08:24
        Thu, Jun 6|Boston - Chicago|Spirit Airlines
        NZD 60NZD 114
        47% OFF
        47% OFF
        NZD 114NZD 60
      • BOS07:00
        2h 33m
        Direct
        ORD08:33
        Tue, Jun 11|Boston - Chicago|Spirit Airlines
        NZD 60NZD 114
        47% OFF
        47% OFF
        NZD 114NZD 60
      • BOS07:00
        2h 33m
        Direct
        ORD08:33
        Wed, Jun 12|Boston - Chicago|Spirit Airlines
        NZD 62NZD 114
        46% OFF
        46% OFF
        NZD 114NZD 62
      • BOS06:10
        11h 25m
        1 stop
        ORD16:35
        Tue, May 14|Boston - Chicago|Spirit Airlines
        NZD 71
        NZD 71
      • BOS06:10
        11h 25m
        1 stop
        ORD16:35
        Wed, May 15|Boston - Chicago|Spirit Airlines
        NZD 71
        NZD 71
      • BOS12:46
        11h 44m
        1 stop
        MDW23:30
        Wed, May 15|Boston - Chicago|Frontier Airlines
        NZD 73
        NZD 73
      • BOS12:41
        11h
        1 stop
        MDW22:41
        Sat, May 11|Boston - Chicago|Frontier Airlines
        NZD 76
        NZD 76
      • BOS10:21
        14h 55m
        1 stop
        MDW00:16
        Tue, May 7|Boston - Chicago|Frontier Airlines
        NZD 77
        NZD 77
      • BOS10:21
        14h 55m
        1 stop
        MDW00:16
        Tue, Apr 30|Boston - Chicago|Frontier Airlines
        NZD 78
        NZD 78
      • BOS08:21
        27h 26m
        1 stop
        ORD10:47
        Mon, May 13|Boston - Chicago|Frontier Airlines
        NZD 78
        NZD 78
      • BOS13:00
        3h 5m
        Direct
        CHI14:00
        Sun, May 5|Boston - Chicago|Spirit Airlines
        Find More Flights
        Find More Flights

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

Searching for the best last minute flight from Boston to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Boston to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from Boston to Chicago

View airlines operating flights 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 NZD 73
Spirit Airlines
From NZD 79
Delta Air Lines
From NZD 84
American Airlines
From NZD 85
Sun Country Airlines
From NZD 141
United Airlines
From NZD 150
Jetblue Airways
From NZD 174
Southwest Airlines
From NZD 255
Alaska Airlines
From NZD 897
ANA airlines

Find more flights and airlines

Alternative Routes from Boston to Chicago

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Boston to Chicago.

  • Cheapest
    Spirit Airlines
    BOS
    10:01
    9h 22m
    1 transfer
    MDW
    18:23
    General Edward Lawrence Logan International Airport - Midway International Airport
    Tue, May 7Spirit Airlines
    NZD 68
  • Spirit Airlines
    BOS
    05:05
    13h 41m
    1 transfer
    ORD
    17:46
    General Edward Lawrence Logan International Airport - O'Hare International Airport
    Tue, May 7Spirit Airlines
    NZD 101
  • Spirit Airlines
    BOS
    05:05
    13h 41m
    1 transfer
    ORD
    17:46
    General Edward Lawrence Logan International Airport - O'Hare International Airport
    Tue, May 7Spirit Airlines
    NZD 101
    Find More Flights

How do I find the cheapest flights?

  • 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 396.

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

    It takes around 2 hours 52 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 25km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14km. 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

NZD 59

Cheapest round-trip ticket price

NZD 124

Off-season for travel

December

Peak season for travel

October

Flight distance

1,371.27km

Average flight time

2 hours 52 minutes

Popular airline

American Airlines

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