Find cheap flights from Boston to Chicago O'Hare Airport

BOS - ORD

Find cheap flights from Boston to Chicago O'Hare Airport

Round-trip
Economy
Boston (BOS)
Chicago O'Hare Intl
Fri 5/29
Fri 6/5
Any month
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Search hundreds of travel sites at once for deals on flights to Chicago O'Hare Airport

Good to know

Low season

January Best time to beat the crowds with an average 18% drop in price.

High season

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

Average price of a round-trip

$149 (avg. price over the last 2 weeks)

Good deal for a round-trip

$190 or less

When to book flights from Boston to Chicago O'Hare Intl

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 $145 or less.
  • The cheapest flight from Boston to Chicago O'Hare Airport was found 74 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 March, April and May. The cheapest month to fly is January.
  • Morning departure is around 11% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking Boston to Chicago O'Hare Airport flights

Are flight prices cheaper from Boston to Chicago O'Hare Airport because of Coronavirus (COVID-19)?

How long does a flight from Boston to Chicago O'Hare Airport take?

How many flights are there between Boston and Chicago O'Hare Airport?

Which airlines provide the cheapest flights from Boston to Chicago O'Hare Airport?

Do I need a passport to fly between Boston and Chicago O'Hare Airport?

Which airlines fly most frequently between Boston and Chicago O'Hare Airport?

What’s the cheapest day of the week to fly Boston to Chicago O'Hare Airport?

How does KAYAK’s flight Price Forecast tool help me choose the right time to buy?

Book cheap flights from Boston to Chicago O'Hare Airport (round-trip)

Airports
Origin
Boston
$49
only
$49
Destination
Chicago
$49
only
$49
Wed, Jul 8
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Wed, Jul 15
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 27m
Trip: 8 days
Based on null reviews
Thu, Aug 20
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Tue, Aug 25
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 27m
Trip: 6 days
Based on null reviews
Thu, Aug 20
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Tue, Aug 25
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 27m
Trip: 6 days
Based on null reviews
Tue, Jul 7
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Tue, Jul 14
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 27m
Trip: 8 days
Based on null reviews
Tue, Aug 4
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Tue, Aug 18
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 27m
Trip: 15 days
Based on null reviews
Wed, Jul 8
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
5h 06m
Wed, Jul 15
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 27m
Trip: 8 days
Based on null reviews
Tue, Jul 7
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Tue, Jul 14
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
6h 07m
Trip: 8 days
Based on null reviews
Wed, Jul 22
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Tue, Jul 28
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 27m
Trip: 7 days
Based on null reviews
Thu, Aug 20
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Tue, Aug 25
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
12h 26m
Trip: 6 days
Based on null reviews
Wed, Jul 8
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Sun, Jul 12
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
11h 45m
Trip: 5 days
Based on null reviews
Tue, Jul 7
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Tue, Jul 14
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
6h 07m
Trip: 8 days
Based on null reviews
Wed, Jul 22
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Tue, Jul 28
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
6h 07m
Trip: 7 days
Based on null reviews
Wed, Jul 8
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Fri, Jul 17
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 27m
Trip: 10 days
Based on null reviews
Tue, Aug 11
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Thu, Aug 20
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 27m
Trip: 10 days
Based on null reviews
Wed, Aug 5
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Tue, Aug 11
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
8h 32m
Trip: 7 days
Based on null reviews
Fri, Aug 21
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Tue, Aug 25
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 27m
Trip: 5 days
Based on null reviews
Wed, Aug 5
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Sun, Aug 9
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 27m
Trip: 5 days
Based on null reviews
Wed, Jul 8
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Sun, Jul 12
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 34m
Trip: 5 days
Based on null reviews
Tue, Aug 4
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Fri, Aug 7
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
2h 27m
Trip: 4 days
Based on null reviews
Wed, Jul 8
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Sun, Jul 12
ORD
Chicago O'Hare Airport
BOS
Boston Logan Airport
7h 48m
Trip: 5 days
Based on null reviews
Show more results

Book cheap flights from Boston to Chicago O'Hare Airport (one-way)

Airports
Origin
Boston
$25
only
$25
Destination
Chicago
$25
only
$25
Wed, Jul 8
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Based on null reviews
Tue, Jul 14
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Based on null reviews
Wed, Aug 12
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Based on null reviews
Wed, Jul 8
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
5h 06m
Based on null reviews
Mon, Jul 6
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
15h 06m
Based on null reviews
Tue, Jul 14
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
5h 06m
Based on null reviews
Mon, Jul 6
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Based on null reviews
Sat, Jul 25
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Based on null reviews
Tue, Jul 14
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
2h 55m
Based on null reviews
Sun, May 24
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
4h 10m
Based on null reviews
Sun, May 31
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
5h 53m
Based on null reviews
Wed, Aug 12
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
15h 06m
Based on null reviews
Mon, Jun 8
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
30h 00m
Based on null reviews
Sat, Jun 6
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
30h 00m
Based on null reviews
Sat, May 30
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
30h 00m
Based on null reviews
Fri, Jun 19
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
30h 00m
Based on null reviews
Tue, Jul 14
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
3h 01m
Based on null reviews
Sun, Jun 14
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
4h 25m
Based on null reviews
Sat, May 30
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
4h 17m
Based on null reviews
Mon, Jul 6
BOS
Boston Logan Airport
ORD
Chicago O'Hare Airport
29h 56m
Based on null reviews
Show more results

Top 4 airlines serving Boston Logan Intl to Chicago O'Hare Intl

Scores according to KAYAK customer reviews

8.2
JetBlue
Overall score based on 19,139 reviews
8.3
Boarding
8.3
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews
Read more about JetBlue
*
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.

Here's why:

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

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

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,
please send us an and someone from our team will get back to you promptly.

^
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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