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Find cheap one-way flights from Chicago to Boston starting at US$50.

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

  • 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 Chicago to Boston?

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 Chicago to Boston

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Delta Air Lines
From US$50
Southwest Airlines
From US$51
Frontier Airlines
From US$57
American Airlines
From US$79
Spirit Airlines
From US$82
Jetblue Airways
From US$86
Sun Country Airlines
From US$128
Alaska Airlines
From US$184
United Airlines
From US$214
ANA airlines

Find more flights and airlines

Find cheap flights from Chicago to Boston by different airports

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

  • Cheapest
    Southwest Airlines
    MDW
    20:05
    2h 10m
    Direct
    BOS
    23:15
    Midway International Airport - General Edward Lawrence Logan International Airport
    Sat, Mar 30Southwest Airlines
    US$51
  • Spirit Airlines
    ORD
    08:21
    9h 12m
    1 transfer
    BOS
    18:33
    O'Hare International Airport - General Edward Lawrence Logan International Airport
    Tue, May 14Spirit Airlines
    US$82
  • Spirit Airlines
    ORD
    08:21
    9h 12m
    1 transfer
    BOS
    18:33
    O'Hare International Airport - General Edward Lawrence Logan International Airport
    Tue, May 14Spirit Airlines
    US$82
    Find More Flights

Frequently Asked Questions

  • When are flight tickets from Chicago (CHI) to Boston (BOS) the cheapest?

    Airlines adjust prices for flights from Chicago to Boston 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 Chicago (CHI) to Boston (BOS) cost?

    According to Trip.com's data, the lowest price is around $275.
  • How long does it take to fly from Chicago (CHI) to Boston (BOS) and what is the distance?

    It takes around 2 hours 26 minutes to fly from Chicago (CHI) to Boston (BOS).
  • What are the most popular airlines that fly from Chicago (CHI) to Boston (BOS)?

Chicago to Boston Flight Information

Cheapest nonstop flight price

$49

Cheapest round-trip ticket price

$95

Off-season for travel

November

Peak season for travel

September