Find cheap flights from Boston to Chicago

BOS - CHI

Find cheap flights from Boston to Chicago

Round-trip
Economy
Boston (BOS)
Chicago All airports
Fri 8/7
Fri 8/14
Any month
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Good to know

Low season

September Best time to beat the crowds with an average 17% drop in price.

High season

July Most popular time to fly with an average 15% increase in price.

Average price of a round-trip

$190 (avg. price over the last 2 weeks)

Good deal for a round-trip

$173 or less

When to book flights from Boston to Chicago

Estimated round-trip price
Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $104 or less.
  • The cheapest flight from Boston to Chicago was found 88 days before departure, on average.
  • Book at least 5 weeks before departure in order to get a below-average price.
  • High season is considered to be June, July and August. The cheapest month to fly is September.
  • Morning departure is around 111% more expensive than an evening flight, on average*.
  • Before your flight from Boston to Chicago, be sure to get a taste of some excellent seafood at Legal's Test Kitchen. This restaurant features an all-day menu, but its specialties are its seafood-inspired dishes like shrimp cocktail and a variety of clam chowders. Located in Terminal A of Boston Logan International Airport, this is a perfect spot to get that last New England-style seafood meal before your flight to the Midwest.
  • There may be nothing that says Boston better than Wahlburgers. Founded and operated by the iconic Wahlberg family, this burger joint is known for its oversized burgers and outrageous onion rings. They are located in Terminal C of Boston Logan International Airport, and they make a great spot to grab a burger and beer before your flight from Boston to Chicago.
  • Flights from Boston to Chicago can be stressful. Why not slow down for a few minutes before your flight with a chair massage or a manicure at BeRelax? Located in Terminal C near Gare C-25 at Boston Logan International Airport, BeRelax also offers waxing and facial care to give you your best look and most relaxed self before your flight.
  • Travelers on flights from Boston to Chicago looking for a convenient hotel need look no further than the Hilton Chicago O'Hare Airport. This on-site property is excellent for business travelers who do not want to bother with the hassle of downtown hotels. The hotel features an indoor pool, an excellent restaurant for steaks and seafood, and a lively sports bar.
  • When looking for a hotel that is conveniently located close to Chicago Midway airport, the Chicago Marriott Midway is an excellent choice. They offer a 24-hour airport shuttle, tasteful decor, an indoor pool, tons of meeting space, a fitness center, wireless internet access, and even a Starbucks coffee shop.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking Boston to Chicago flights

Which airlines have a flexible cancellation policy for flights from Boston Logan Intl to Chicago due to COVID-19?

Which airlines apply social distancing measures on flights from Boston Logan Intl to Chicago due to COVID-19?

How long does a flight from Boston to Chicago take?

How many flights are there between Boston and Chicago?

Which airlines provide the cheapest flights from Boston to Chicago?

Do I need a passport to fly between Boston and Chicago?

Which airlines fly most frequently between Boston and Chicago?

What’s the cheapest day of the week to fly Boston to Chicago?

Which airports will I be using when flying from Boston to Chicago?

If I want to use mass transit to get to Boston Logan International Airport, what is my best choice?

Are there pet relief areas at Boston Logan International Airport?

If I am being picked up at Chicago O'Hare International Airport, where is the best place to meet my ride?

Where can I rent a car at Chicago O'Hare International Airport?

How does KAYAK find such low prices on flights from Boston to Chicago?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Boston to Chicago?

What is the Hacker Fare option on flights from Boston to Chicago?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Boston to Chicago?

Top 4 airlines serving Boston Logan Intl to Chicago

Scores according to KAYAK customer reviews

8.2
JetBlue
Overall score based on 19,205 reviews
8.3
Boarding
8.3
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews
Read more about JetBlue

Book cheap flights from Boston to Chicago

Recent round-trip flight deals

8/7
Fri
nonstop
Spirit Airlines
2h 57m
BOS - ORD
8/21
Fri
nonstop
Spirit Airlines
2h 25m
ORD - BOS
8/9
Sun
nonstop
Major Airline
2h 42m
BOS - ORD
8/14
Fri
nonstop
Major Airline
2h 26m
ORD - BOS
8/1
Sat
nonstop
Spirit Airlines
2h 52m
BOS - ORD
8/3
Mon
nonstop
Spirit Airlines
2h 21m
ORD - BOS
7/23
Thu
nonstop
Spirit Airlines
2h 52m
BOS - ORD
7/26
Sun
nonstop
Spirit Airlines
2h 21m
ORD - BOS
8/7
Fri
nonstop
Spirit Airlines
2h 57m
BOS - ORD
8/14
Fri
nonstop
Spirit Airlines
2h 25m
ORD - BOS
9/17
Thu
1 stop
Delta
6h 25m
BOS - MDW
9/20
Sun
1 stop
Delta
7h 34m
MDW - BOS
8/6
Thu
nonstop
Spirit Airlines
2h 57m
BOS - ORD
8/9
Sun
nonstop
Spirit Airlines
2h 25m
ORD - BOS
8/7
Fri
nonstop
Spirit Airlines
2h 57m
BOS - ORD
8/21
Fri
1 stop
Spirit Airlines
4h 53m
ORD - BOS
8/13
Thu
nonstop
Spirit Airlines
2h 57m
BOS - ORD
8/20
Thu
1 stop
Spirit Airlines
4h 53m
ORD - BOS
7/27
Mon
1 stop
Spirit Airlines
9h 30m
BOS - ORD
8/3
Mon
nonstop
Spirit Airlines
2h 21m
ORD - BOS
7/24
Fri
nonstop
Spirit Airlines
2h 52m
BOS - ORD
8/3
Mon
1 stop
Spirit Airlines
9h 32m
ORD - BOS
8/4
Tue
nonstop
Spirit Airlines
2h 52m
BOS - ORD
8/22
Sat
nonstop
Spirit Airlines
2h 25m
ORD - BOS
Show more results

Recent one-way flight deals

8/1
Sat
nonstop
Spirit Airlines
2h 52m
BOS - ORD
7/26
Sun
nonstop
Major Airline
2h 49m
BOS - ORD
8/7
Fri
nonstop
Spirit Airlines
2h 57m
BOS - ORD
7/29
Wed
1 stop
Multiple Airlines
8h 59m
BOS - ORD
8/21
Fri
nonstop
Spirit Airlines
2h 57m
BOS - ORD
9/13
Sun
1 stop
Delta
5h 26m
BOS - MDW
7/26
Sun
1 stop
Spirit Airlines
9h 30m
BOS - ORD
9/4
Fri
nonstop
Spirit Airlines
2h 57m
BOS - ORD
9/4
Fri
1 stop
Allegiant Air
6h 28m
BOS - MDW
7/31
Fri
1 stop
Multiple Airlines
9h 43m
BOS - ORD
7/23
Thu
nonstop
Spirit Airlines
2h 52m
BOS - ORD
8/17
Mon
1 stop
Multiple Airlines
7h 39m
BOS - ORD
7/30
Thu
1 stop
Multiple Airlines
19h 58m
BOS - ORD
8/12
Wed
1 stop
Multiple Airlines
24h 06m
BOS - ORD
7/26
Sun
1 stop
Spirit Airlines
9h 30m
BOS - ORD
7/23
Thu
1 stop
Major Airline
5h 34m
BOS - ORD
7/27
Mon
1 stop
Multiple Airlines
21h 41m
BOS - ORD
8/28
Fri
nonstop
Spirit Airlines
2h 57m
BOS - ORD
Show more results
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

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If you have more questions or if you have a bad price to report to us,
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^
The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.
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