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Cheap flights from Chicago O'Hare Intl Airport to Boston from $53

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 10/16. 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

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago O'Hare Intl Airport to Boston.
JetBlue Logo
10:50 am - 2:18 pmORD-BOS
2h 28mnonstop
JetBlue Logo
4:30 pm - 6:36 pmBOS-ORD
3h 06mnonstop
$112JetBlue
Find Deal
Wed, May 7 - Wed, May 7
American Airlines Logo
11:49 am - 3:10 pmORD-BOS
2h 21mnonstop
American Airlines Logo
5:15 am - 7:15 amBOS-ORD
3h 00mnonstop
$116American Airlines
Find Deal
Wed, May 28 - Sun, Jun 1
United Airlines Logo
7:10 am - 10:38 amORD-BOS
2h 28mnonstop
United Airlines Logo
7:45 am - 9:42 amBOS-ORD
2h 57mnonstop
$117United Airlines
Find Deal
Sat, May 10 - Tue, May 13
Spirit Airlines Logo
12:41 pm - 11:29 pmORD-BOS
9h 48m1 stop
Spirit Airlines Logo
3:49 pm - 11:04 pmBOS-ORD
8h 15m1 stop
$128Spirit Airlines
Find Deal
Tue, May 13 - Wed, May 21
Spirit Airlines Logo
12:41 pm - 11:29 pmORD-BOS
9h 48m1 stop
Spirit Airlines Logo
3:49 pm - 11:04 pmBOS-ORD
8h 15m1 stop
$134Spirit Airlines
Find Deal
Wed, May 14 - Tue, May 20
Southwest Logo
4:00 pm - 12:05 amORD-BOS
7h 05m1 stop
Southwest Logo
8:30 am - 4:25 pmBOS-ORD
8h 55m1 stop
$136Southwest
Find Deal
Fri, Jun 6 - Tue, Jun 10
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
United Airlines Logo
6:00 am - 7:58 amBOS-ORD
2h 58mnonstop
$137United Airlines
Find Deal
Fri, May 30 - Sun, Jun 1
Southwest Logo
4:00 pm - 12:05 amORD-BOS
7h 05m1 stop
Southwest Logo
5:50 am - 1:05 pmBOS-ORD
8h 15m1 stop
$142Southwest
Find Deal
Fri, Jun 6 - Mon, Jun 9
Delta Logo
6:59 pm - 10:45 pmORD-BOS
2h 46mnonstop
Delta Logo
7:20 am - 9:18 amBOS-ORD
2h 58mnonstop
$177Delta
Find Deal
Thu, Jun 19 - Mon, Jun 23
Delta Logo
10:18 am - 1:51 pmORD-BOS
2h 33mnonstop
Delta Logo
8:30 am - 10:22 amBOS-ORD
2h 52mnonstop
$179Delta
Find Deal
Wed, Jul 2 - Sat, Jul 5

Frontier flights from Chicago O'Hare Intl Airport to Boston

Our best Frontier deals on Chicago O'Hare Intl Airport to Boston flight tickets
Frontier
May 17
ORD4:15 pmChicago O'Hare Intl
7h 29m
1 stop
BOS12:44 amBoston Logan Intl
May 24
BOS9:49 amBoston Logan Intl
10h 59m
1 stop
ORD7:48 pmChicago O'Hare Intl
Frontier
May 10
ORD4:15 pmChicago O'Hare Intl
7h 29m
1 stop
BOS12:44 amBoston Logan Intl
May 11
BOS10:14 amBoston Logan Intl
28h 27m
1 stop
ORD1:41 pmChicago O'Hare Intl
Frontier
May 10
ORD4:15 pmChicago O'Hare Intl
7h 29m
1 stop
BOS12:44 amBoston Logan Intl
May 11
BOS10:14 amBoston Logan Intl
28h 27m
1 stop
ORD1:41 pmChicago O'Hare Intl

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
May 28
ORD11:49 amChicago O'Hare Intl
2h 21m
BOS3:10 pmBoston Logan Intl
Jun 1
BOS5:15 amBoston Logan Intl
3h 00m
ORD7:15 amChicago O'Hare Intl
American Airlines
May 10
ORD8:21 amChicago O'Hare Intl
2h 22m
BOS11:43 amBoston Logan Intl
May 11
BOS6:35 amBoston Logan Intl
2h 56m
ORD8:31 amChicago O'Hare Intl
American Airlines
May 20
ORD7:37 amChicago O'Hare Intl
2h 35m
BOS11:12 amBoston Logan Intl
May 27
BOS8:51 pmBoston Logan Intl
3h 01m
ORD10:52 pmChicago O'Hare Intl

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 $196. If you aren’t able to travel during the month of September, then book flights to Boston from Chicago O'Hare Intl Airport during August instead. Flights to Boston in August, 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 Wednesday when prices can be found for as low as $250. 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 $326.

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 $199. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the afternoon is when there is more demand to fly to Boston, so prices are often more expensive at around $297 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 6 weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $239 when searching 6 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 $200 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 April 2025, prices for Chicago O'Hare Intl Airport to Boston flights are approximately 27% more expensive 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

$53

Fastest flight time

2h 21m

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 $53. The best round-trip flight deal from Chicago O'Hare Intl Airport to Boston found on momondo in the last 72 hours is $112.
The fastest flight from Chicago O'Hare Intl Airport to Boston takes 2h 21m
Direct flights go from Chicago O'Hare Intl Airport to Boston every day.
There is 1 airport near Boston: Boston Logan Intl (BOS)

  • 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 21m 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 $38Free CancellationRating
6.3
7,940 reviews
Search Spirit Airlines flights
FrontierPriceFrom $69Free CancellationRating
5.9
3,283 reviews
Search Frontier flights
JetBluePriceFrom $79Free CancellationRating
7.3
2,924 reviews
Search JetBlue flights
DeltaPriceFrom $88Free CancellationRating
8.0
7,920 reviews
Search Delta flights
American AirlinesPriceFrom $137Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $140Free CancellationRating
7.4
8,685 reviews
Search United Airlines flights
SouthwestPriceFrom $214Free CancellationRating
8.0
4,287 reviews
Search Southwest flights
  • Delta Flights From Chicago O'Hare Intl Airport to Boston

    Across 16 Delta flights from Chicago O'Hare Intl Airport to Boston this week, the average price was $231, with the best Delta deals starting from $88 round-trip. 7,920 users have rated Delta on momondo, with an average score of 8.0/10.

  • 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 $140 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $292. United Airlines operates 33 flights to Boston from Chicago O'Hare Intl Airport in an average week. Users have rated it 7.4/10 across 8,685 reviews.


Traveling to a place near Boston?

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

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.


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