Find cheap flights from Chicago to Boston

CHI - BOS

Find cheap flights from Chicago to Boston

Round-trip
Economy
Chicago (CHI)
Boston Logan Intl
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 15% drop in price.

High season

July Most popular time to fly with an average 18% increase in price.

Average price of a round-trip

$179 (avg. price over the last 2 weeks)

Good deal for a round-trip

$172 or less

When to book flights from Chicago to Boston

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 $102 or less.
  • The cheapest flight from Chicago to Boston was found 60 days before departure, on average.
  • Book at least 2 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 76% more expensive than an evening flight, on average*.
  • If you’re looking at flights from Chicago to Boston, there are two different airports that you can fly out of. O'Hare International Airport is the largest airport in the region and harbors a high concentration of flights, while Chicago Midway International Airport is a smaller choice that is located only several miles from the city’s downtown.
  • Hoping to have a direct flight from Chicago to Boston? There are several major airlines that you can choose from. Southwest Airlines is popular amongst travelers with a large amount of luggage, as they allow you to check up to two bags for free, while Delta Airlines offers many upgrade options for those who would prefer more comfortable chairs or extra legroom.
  • For those that are traveling with kids, make sure to stop by one of the several children’s play areas located in Logan International Airport. These play areas are free for all travelers and feature a variety of toys, games, and activities that will help kids (and their parents) unwind after a long day of traveling.
  • To help pass the time before your flight takes off from O'Hare International Airport, see if you can access one of the airport’s private lounges. American, United, and Delta Airlines all have lounges in Chicago, and they often provide complimentary or reduced price access passes for their customers.
  • Flying can sometimes be stressful, so make sure you’re taking the time to unwind before boarding your plane. O'Hare International Airport has both a fitness club and a yoga room, both of which are perfect ways to let off some steam and relax before embarking on a day of traveling.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking Chicago to Boston flights

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

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

How long does a flight from Chicago to Boston take?

How many flights are there between Chicago and Boston?

Which airlines provide the cheapest flights from Chicago to Boston?

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

Which airlines fly most frequently between Chicago and Boston?

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

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

Does Logan International Airport have pet relief areas?

What are good hotels near Logan International Airport?

What dining options are there in Chicago Midway International Airport?

Does Logan International Airport have a prayer room?

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

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

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

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

Top 5 airlines serving Chicago to Boston Logan Intl

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 Chicago to Boston

Recent round-trip flight deals

8/13
Thu
nonstop
Spirit Airlines
2h 25m
ORD - BOS
8/17
Mon
nonstop
Spirit Airlines
2h 57m
BOS - ORD
8/21
Fri
nonstop
Major Airline
2h 26m
ORD - BOS
8/23
Sun
nonstop
Major Airline
2h 42m
BOS - ORD
7/29
Wed
nonstop
Spirit Airlines
2h 26m
ORD - BOS
7/31
Fri
nonstop
Spirit Airlines
2h 52m
BOS - ORD
8/7
Fri
nonstop
Spirit Airlines
2h 25m
ORD - BOS
8/9
Sun
nonstop
Spirit Airlines
2h 57m
BOS - ORD
7/31
Fri
nonstop
Spirit Airlines
2h 21m
ORD - BOS
8/6
Thu
nonstop
Spirit Airlines
2h 57m
BOS - ORD
9/8
Tue
1 stop
Delta
5h 15m
MDW - BOS
9/9
Wed
1 stop
Delta
4h 35m
BOS - MDW
9/19
Sat
nonstop
Spirit Airlines
2h 31m
ORD - BOS
9/26
Sat
nonstop
Spirit Airlines
2h 33m
BOS - ORD
7/29
Wed
nonstop
Spirit Airlines
2h 26m
ORD - BOS
7/29
Wed
1 stop
Spirit Airlines
14h 41m
BOS - ORD
8/13
Thu
1 stop
Spirit Airlines
4h 53m
ORD - BOS
8/17
Mon
nonstop
Spirit Airlines
2h 57m
BOS - ORD
8/7
Fri
1 stop
Spirit Airlines
9h 00m
ORD - BOS
8/9
Sun
nonstop
Spirit Airlines
2h 57m
BOS - ORD
8/29
Sat
1 stop
Spirit Airlines
9h 00m
ORD - BOS
9/5
Sat
nonstop
Spirit Airlines
2h 57m
BOS - ORD
8/4
Tue
1 stop
Spirit Airlines
12h 17m
ORD - BOS
8/10
Mon
nonstop
Spirit Airlines
2h 57m
BOS - ORD
Show more results

Recent one-way flight deals

7/29
Wed
nonstop
Spirit Airlines
2h 26m
ORD - BOS
7/29
Wed
nonstop
Major Airline
2h 25m
ORD - BOS
7/31
Fri
nonstop
Spirit Airlines
2h 21m
ORD - BOS
7/26
Sun
nonstop
Allegiant Air
2h 20m
ORD - BOS
8/12
Wed
nonstop
Spirit Airlines
2h 25m
ORD - BOS
8/10
Mon
1 stop
Cape Air
5h 22m
ORD - BOS
7/29
Wed
1 stop
Multiple Airlines
18h 11m
ORD - BOS
9/20
Sun
1 stop
Delta
5h 28m
MDW - BOS
7/26
Sun
1 stop
Spirit Airlines
4h 53m
ORD - BOS
9/7
Mon
nonstop
Spirit Airlines
2h 25m
ORD - BOS
8/15
Sat
nonstop
Spirit Airlines
2h 25m
ORD - BOS
7/23
Thu
1 stop
Delta
4h 02m
ORD - BOS
7/31
Fri
1 stop
Multiple Airlines
7h 04m
ORD - BOS
7/31
Fri
2 stops
Multiple Airlines
13h 38m
ORD - BOS
9/7
Mon
1 stop
Delta
5h 46m
ORD - BOS
7/29
Wed
1 stop
Major Airline
5h 55m
ORD - BOS
7/25
Sat
2 stops
Multiple Airlines
15h 13m
ORD - BOS
Show more results
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

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At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

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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