Worldwide Coverage

Worldwide Coverage

Flights to over 5,000 cities
One-stop Service Guarantee

One-stop Service Guarantee

Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment

Secure Payment

Convenient & reliable booking and payment system

Find cheap one-way flights from Boston to Chicago starting at US$38.

Book one-way or return flights from Boston to Chicago from as little as US$38. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip

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

When is the cheapest time to book flights 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.
Cheapest airlines 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 US$38
Southwest Airlines
From US$48
Jetblue Airways
From US$69
Spirit Airlines
From US$82
Sun Country Airlines
From US$128
Delta Air Lines
From US$138
Alaska Airlines
From US$180
Allegiant Air
From US$208
United Airlines
From US$209
American Airlines
From US$263
ANA airlines

Find more flights and airlines

Find cheap flights from Boston to Chicago by different airports

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

  • Cheapest
    Frontier Airlines
    BOS
    08:21
    9h 40m
    1 transfer
    MDW
    17:01
    General Edward Lawrence Logan International Airport - Midway International Airport
    Wed, Mar 20Frontier Airlines
    US$38
  • American Airlines
    BOS
    06:55
    2h 59m
    Direct
    ORD
    08:54
    General Edward Lawrence Logan International Airport - O'Hare International Airport
    Thu, Mar 21American Airlines
    US$263
  • Southern Airways Express
    BNH
    09:20
    12h 27m
    1 transfer
    ORD
    20:47
    Hartford Barnes Airport - O'Hare International Airport
    Sat, Apr 13Southern Airways Express
    US$510
  • Southern Airways Express
    BNH
    09:20
    12h 27m
    1 transfer
    ORD
    20:47
    Hartford Barnes Airport - O'Hare International Airport
    Sat, Apr 13Southern Airways Express
    US$510
    Find More Flights

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 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 $275.
  • How long does it take to fly from Boston (BOS) to Chicago (CHI) and what is the distance?

    It takes around 2 hours 56 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)?

    Airlines with flights from Boston (BOS) to Chicago (CHI): American Airlines, United Airlines, Qatar Airways, Icelandair, Alaska Airlines, Korean Air and Jetblue Airways.

Boston to Chicago Flight Information

Cheapest nonstop flight price

$38

Cheapest round-trip ticket price

$102

Off-season for travel

December

Peak season for travel

June