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Cheap flights from Chicago O'Hare Intl Airport to Boston from $55

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 8/5. 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

Spirit Airlines Logo
10:00 am - 11:03 pmORD-BOS
12h 03m1 stop
Spirit Airlines Logo
6:15 am - 3:31 pmBOS-ORD
10h 16m1 stop
$112Spirit Airlines
Find Deal
Tue, Aug 5 - Wed, Aug 6
Spirit Airlines Logo
5:05 am - 7:34 pmORD-BOS
13h 29m1 stop
Spirit Airlines Logo
8:39 pm - 8:55 amBOS-ORD
13h 16m1 stop
$114Spirit Airlines
Find Deal
Tue, Aug 5 - Wed, Aug 6
American Airlines Logo
8:25 pm - 11:59 pmORD-BOS
2h 34mnonstop
American Airlines Logo
11:00 am - 1:00 pmBOS-ORD
3h 00mnonstop
$117American Airlines
Find Deal
Tue, Sep 2 - Wed, Sep 3
American Airlines Logo
6:15 am - 9:43 amORD-BOS
2h 28mnonstop
American Airlines Logo
2:45 pm - 4:49 pmBOS-ORD
3h 04mnonstop
$126American Airlines
Find Deal
Wed, Aug 27 - Wed, Sep 3
JetBlue Logo
8:40 am - 12:04 pmORD-BOS
2h 24mnonstop
JetBlue Logo
7:00 am - 8:56 amBOS-ORD
2h 56mnonstop
$127JetBlue
Find Deal
Wed, Aug 27 - Wed, Sep 3
JetBlue Logo
9:42 am - 1:10 pmORD-BOS
2h 28mnonstop
JetBlue Logo
7:00 am - 8:57 amBOS-ORD
2h 57mnonstop
$128JetBlue
Find Deal
Thu, Sep 4 - Sun, Sep 7
United Airlines Logo
8:05 pm - 11:32 pmORD-BOS
2h 27mnonstop
United Airlines Logo
7:04 pm - 11:41 pmBOS-ORD
5h 37m1 stop
$143United Airlines
Find Deal
Wed, Aug 6 - Tue, Aug 12
Delta Logo
7:25 am - 10:55 amORD-BOS
2h 30mnonstop
Delta Logo
11:55 am - 1:43 pmBOS-ORD
2h 48mnonstop
$147Delta
Find Deal
Tue, Sep 16 - Sat, Sep 27
Delta Logo
2:10 pm - 5:54 pmORD-BOS
2h 44mnonstop
Delta Logo
7:20 am - 9:15 amBOS-ORD
2h 55mnonstop
$155Delta
Find Deal
Sat, Aug 30 - Tue, Sep 9
United Airlines Logo
7:49 pm - 11:16 pmORD-BOS
2h 27mnonstop
United Airlines Logo
6:07 am - 8:05 amBOS-ORD
2h 58mnonstop
$175United Airlines
Find Deal
Fri, Aug 8 - Mon, Aug 11

Southwest flights from Chicago O'Hare Intl Airport to Boston

Our best Southwest deals on Chicago O'Hare Intl Airport to Boston flight tickets
Southwest
Aug 30
ORD2:55 pmChicago O'Hare Intl
5h 00m
1 stop
BOS8:55 pmBoston Logan Intl
Sep 2
BOS5:20 amBoston Logan Intl
8h 25m
1 stop
ORD12:45 pmChicago O'Hare Intl
$136
Find similar
Southwest
Aug 30
ORD2:55 pmChicago O'Hare Intl
5h 00m
1 stop
BOS8:55 pmBoston Logan Intl
Sep 1
BOS5:35 amBoston Logan Intl
8h 10m
1 stop
ORD12:45 pmChicago O'Hare Intl
$142
Find similar
Southwest
Sep 4
ORD1:50 pmChicago O'Hare Intl
7h 25m
1 stop
BOS10:15 pmBoston Logan Intl
Sep 7
BOS5:45 amBoston Logan Intl
8h 00m
1 stop
ORD12:45 pmChicago O'Hare Intl
$146
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Spirit Airlines flights from Chicago O'Hare Intl Airport to Boston

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Boston flight tickets
Spirit Airlines
Aug 5
ORD10:00 amChicago O'Hare Intl
12h 03m
1 stop
BOS11:03 pmBoston Logan Intl
Aug 6
BOS6:15 amBoston Logan Intl
10h 16m
1 stop
ORD3:31 pmChicago O'Hare Intl
$112
Find similar
Spirit Airlines
Aug 5
ORD5:05 amChicago O'Hare Intl
13h 29m
1 stop
BOS7:34 pmBoston Logan Intl
Aug 6
BOS8:39 pmBoston Logan Intl
13h 16m
1 stop
ORD8:55 amChicago O'Hare Intl
$114
Find similar
Spirit Airlines
Aug 5
ORD10:00 amChicago O'Hare Intl
8h 30m
1 stop
BOS7:30 pmBoston Logan Intl
Aug 6
BOS8:39 pmBoston Logan Intl
13h 16m
1 stop
ORD8:55 amChicago O'Hare Intl
$115
Find similar

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 $177. 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 $207.

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 Saturday when prices can be found for as low as $237. 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 $299.

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 $210. 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 $278 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 $228 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 $190 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 July 2025, prices for Chicago O'Hare Intl Airport to Boston flights are approximately 28% 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

$55

Fastest flight time

2h 19m

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 $55. 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 19m
Direct flights go from Chicago O'Hare Intl Airport to Boston every day.
There is 1 airport near Boston: Boston Logan Intl (BOS)
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  • 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 19m 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
8,047 reviews
Search Spirit Airlines flights
JetBluePriceFrom $78Free CancellationRating
7.3
2,908 reviews
Search JetBlue flights
DeltaPriceFrom $91Free CancellationRating
8.0
7,953 reviews
Search Delta flights
FrontierPriceFrom $100Free CancellationRating
5.9
3,260 reviews
Search Frontier flights
American AirlinesPriceFrom $126Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $129Free CancellationRating
7.4
8,856 reviews
Search United Airlines flights
SouthwestPriceFrom $156Free CancellationRating
8.0
4,243 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 $220, with the best Delta deals starting from $91 round-trip. 7,956 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 $129 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $280. United Airlines operates 42 flights to Boston from Chicago O'Hare Intl Airport in an average week. Users have rated it 7.4/10 across 8,858 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
York Beach
Plymouth
Cambridge
Kennebunkport
Nashua
Narragansett
Laconia
Brockton
Concord
Gloucester
South Yarmouth
Everett
Wells
Falmouth
Warwick

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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