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Cheap flights from Chicago O'Hare Intl Airport to Boston from $69

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to Boston departing on 9/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago O'Hare Intl Airport to Boston (ORD-BOS)

Cheap round-trip flights

Logo
11:57 am - 11:57 pmORD-BOS
11h 00m1 stop
Logo
8:38 am - 4:45 pmBOS-ORD
9h 07m1 stop
$129
Find Deal
Wed, Sep 17 - Sat, Sep 20
JetBlue Logo
10:08 am - 1:37 pmORD-BOS
2h 29mnonstop
JetBlue Logo
7:09 am - 9:22 amBOS-ORD
3h 13mnonstop
$130JetBlue
Find Deal
Sat, Oct 18 - Sat, Oct 25
Spirit Airlines Logo
11:57 am - 11:57 pmORD-BOS
11h 00m1 stop
Spirit Airlines Logo
3:00 pm - 10:48 pmBOS-ORD
8h 48m1 stop
$135Spirit Airlines
Find Deal
Wed, Sep 17 - Tue, Sep 23
Spirit Airlines Logo
11:57 am - 11:57 pmORD-BOS
11h 00m1 stop
Spirit Airlines Logo
3:00 pm - 10:48 pmBOS-ORD
8h 48m1 stop
$136Spirit Airlines
Find Deal
Wed, Sep 17 - Sat, Sep 20
Delta Logo
7:25 am - 10:55 amORD-BOS
2h 30mnonstop
Delta Logo
7:25 am - 9:15 amBOS-ORD
2h 50mnonstop
$137Delta
Find Deal
Wed, Sep 17 - Sun, Sep 21
American Airlines Logo
5:00 pm - 8:22 pmORD-BOS
2h 22mnonstop
American Airlines Logo
7:14 pm - 9:20 pmBOS-ORD
3h 06mnonstop
$141American Airlines
Find Deal
Sat, Nov 22 - Mon, Nov 24
United Airlines Logo
7:30 am - 11:01 amORD-BOS
2h 31mnonstop
United Airlines Logo
8:27 pm - 10:15 pmBOS-ORD
2h 48mnonstop
$150United Airlines
Find Deal
Mon, Sep 8 - Mon, Sep 15
Delta Logo
7:10 pm - 10:45 pmORD-BOS
2h 35mnonstop
Delta Logo
4:10 pm - 6:10 pmBOS-ORD
3h 00mnonstop
$155Delta
Find Deal
Fri, Oct 17 - Wed, Oct 22
United Airlines Logo
9:20 pm - 12:50 amORD-BOS
2h 30mnonstop
United Airlines Logo
8:47 pm - 10:35 pmBOS-ORD
2h 48mnonstop
$157United Airlines
Find Deal
Fri, Sep 26 - Mon, Sep 29
American Airlines Logo
7:32 pm - 11:02 pmORD-BOS
2h 30mnonstop
American Airlines Logo
5:24 am - 7:25 amBOS-ORD
3h 01mnonstop
$165American Airlines
Find Deal
Sat, Oct 11 - Mon, Oct 13

American Airlines flights from Chicago O'Hare Intl Airport to Boston

Our best American Airlines deals on Chicago O'Hare Intl Airport to Boston flight tickets
American Airlines
Sep 4
ORD8:25 pmChicago O'Hare Intl
2h 28m
BOS11:53 pmBoston Logan Intl
Sep 7
BOS5:00 amBoston Logan Intl
2h 51m
ORD6:51 amChicago O'Hare Intl
$128
Find similar
American Airlines
Nov 22
ORD5:00 pmChicago O'Hare Intl
2h 22m
BOS8:22 pmBoston Logan Intl
Nov 24
BOS7:14 pmBoston Logan Intl
3h 06m
ORD9:20 pmChicago O'Hare Intl
$141
Find similar
American Airlines
Oct 11
ORD7:32 pmChicago O'Hare Intl
2h 30m
BOS11:02 pmBoston Logan Intl
Oct 13
BOS5:24 amBoston Logan Intl
3h 01m
ORD7:25 amChicago O'Hare Intl
$165
Find similar

United Airlines flights from Chicago O'Hare Intl Airport to Boston

Our best United Airlines deals on Chicago O'Hare Intl Airport to Boston flight tickets
United Airlines
Sep 5
ORD3:48 pmChicago O'Hare Intl
2h 31m
BOS7:19 pmBoston Logan Intl
Sep 6
BOS12:30 pmBoston Logan Intl
2h 50m
ORD2:20 pmChicago O'Hare Intl
$137
Find similar
United Airlines
Sep 8
ORD7:30 amChicago O'Hare Intl
2h 31m
BOS11:01 amBoston Logan Intl
Sep 15
BOS8:27 pmBoston Logan Intl
2h 48m
ORD10:15 pmChicago O'Hare Intl
$150
Find similar
United Airlines
Sep 26
ORD9:20 pmChicago O'Hare Intl
2h 30m
BOS12:50 amBoston Logan Intl
Sep 29
BOS8:47 pmBoston Logan Intl
2h 48m
ORD10:35 pmChicago O'Hare Intl
$157
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to Boston that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 28, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/17

11:57 am-11:57 pm

1 stop11h 00m

Boston Logan Intl

Sat 9/20

8:38 am-4:45 pm

1 stop9h 07m

$129

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 10/18

10:08 am-1:37 pm

Nonstop2h 29m

Boston Logan Intl

Sat 10/25

7:09 am-9:22 am

Nonstop3h 13m

$130

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/17

11:57 am-11:57 pm

1 stop11h 00m

Boston Logan Intl

Tue 9/23

3:00 pm-10:48 pm

1 stop8h 48m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/17

11:57 am-11:57 pm

1 stop11h 00m

Boston Logan Intl

Sat 9/20

3:00 pm-10:48 pm

1 stop8h 48m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/17

7:25 am-10:55 am

Nonstop2h 30m

Boston Logan Intl

Sun 9/21

7:25 am-9:15 am

Nonstop2h 50m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 11/22

5:00 pm-8:22 pm

Nonstop2h 22m

Boston Logan Intl

Mon 11/24

7:14 pm-9:20 pm

Nonstop3h 06m

$141

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 9/8

7:30 am-11:01 am

Nonstop2h 31m

Boston Logan Intl

Mon 9/15

8:27 pm-10:15 pm

Nonstop2h 48m

$150

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 10/17

7:10 pm-10:45 pm

Nonstop2h 35m

Boston Logan Intl

Wed 10/22

4:10 pm-6:10 pm

Nonstop3h 00m

$155

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 9/26

9:20 pm-12:50 am

Nonstop2h 30m

Boston Logan Intl

Mon 9/29

8:47 pm-10:35 pm

Nonstop2h 48m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 10/11

7:32 pm-11:02 pm

Nonstop2h 30m

Boston Logan Intl

Mon 10/13

5:24 am-7:25 am

Nonstop3h 01m

$165

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Boston from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Boston

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Boston?

In general, September is the cheapest month to fly from Chicago O'Hare Intl Airport to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $178. If you aren’t able to travel during the month of September, then book flights to Boston from Chicago O'Hare Intl Airport during January instead. Flights to Boston in January, while not as cheap as those in September, still average around $209.

What is the cheapest day to depart on your flight to Boston?

The cheapest day to depart from Chicago O'Hare Intl Airport to Boston is on a Thursday when prices can be found for as low as $241. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Sunday is $304.

What is the cheapest time of day to depart on your flight to Boston?

According to our data, the cheapest time of day to fly to Boston is in the evening. momondo users have found flights departing from Chicago O'Hare Intl Airport to Boston in the evening for as low as $227. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. At noon is when there is more demand to fly to Boston, so prices are often more expensive at around $288 per ticket.

What is the cheapest Chicago O'Hare Intl to Boston Logan Intl flight route?

Fly from Chicago O'Hare Intl to Boston Logan Intl for the best Chicago O'Hare Intl - Boston Logan Intl flight prices

How far in advance should I book a flight to Boston?

You are more likely to see cheaper flights to Boston from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $230 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Chicago O'Hare Intl Airport for as low as $188 on momondo.

What cabin class options are available on Chicago O'Hare Intl to Boston Logan Intl flights?

There are 4 cabin classes available to choose from on Chicago O'Hare Intl to Boston Logan Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago O'Hare Intl Airport to Boston flight prices changed over time?

As of August 2025, prices for Chicago O'Hare Intl Airport to Boston flights are approximately 20% cheaper when compared to flights at the same time last year.

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

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago O'Hare Intl Airport to Boston according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago O'Hare Intl Airport to Boston (ORD to BOS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Boston

Best Price Found

$113

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Boston

1 airport
The best one-way flight to Boston from Chicago O'Hare Intl Airport in the past 72 hours is $113. The best round-trip flight deal from Chicago O'Hare Intl Airport to Boston found on momondo in the last 72 hours is $162.
The fastest flight from Chicago O'Hare Intl Airport to Boston takes 2h 15m
Direct flights go from Chicago O'Hare Intl Airport to Boston every day.
There is 1 airport near Boston: Boston Logan Intl (BOS)
Search flight deals

  • How far is Chicago O'Hare Intl to Boston Logan Intl by plane?

    A flight from Chicago O'Hare Intl to Boston Logan Intl will travel around 861.0 mi. 2h 20m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Boston Logan Intl Airport?

    Prices for flights from Chicago O'Hare Intl Airport to Boston Logan Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Boston Logan Intl Airport?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Boston Logan Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago O'Hare Intl Airport to Boston Logan Intl Airport.

  • What documentation or ID do you need to fly to Boston Logan Intl Airport?

    The required travel and health documents for your Boston Logan Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Boston Logan Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago O'Hare Intl Airport to Boston?

  • What is the most popular airline from Chicago O'Hare Intl Airport to Boston?

Best airlines flying from Chicago O'Hare Intl Airport to Boston

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Boston with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $35Free CancellationRating
6.3
8,028 reviews
Search Spirit Airlines flights
JetBluePriceFrom $77Free CancellationRating
7.2
2,920 reviews
Search JetBlue flights
DeltaPriceFrom $92Free CancellationRating
7.9
7,977 reviews
Search Delta flights
FrontierPriceFrom $100Free CancellationRating
5.8
3,204 reviews
Search Frontier flights
American AirlinesPriceFrom $119Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $128Free CancellationRating
7.4
8,944 reviews
Search United Airlines flights
SouthwestPriceFrom $156Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

  • Delta Flights From Chicago O'Hare Intl Airport to Boston

    Across 6 Delta flights from Chicago O'Hare Intl Airport to Boston this week, the average price was $222, with the best Delta deals starting from $92 round-trip. 7,977 users have rated Delta on momondo, with an average score of 7.9/10.

  • United Airlines Flights From Chicago O'Hare Intl Airport to Boston

    United Airlines is also a popular choice for this route. United Airlines flight deals for Chicago O'Hare Intl Airport to Boston start from as low as $128 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $283. United Airlines operates 37 flights to Boston from Chicago O'Hare Intl Airport in an average week. Users have rated it 7.4/10 across 8,944 reviews.

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Hampton Beach
Salem
Ogunquit
Old Orchard Beach
Hampton
York Beach
Plymouth
Kennebunkport
Cambridge
Narragansett
Nashua
South Yarmouth
Gloucester
Brockton
Laconia
Concord
Falmouth
Everett
Wells
Sturbridge

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Boston?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Boston. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Boston with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Boston from Chicago with this policy.

How can momondo help me find flights from Chicago to Boston?

Once you have performed a search for Chicago to Boston flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Boston right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Boston from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Boston trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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