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Cheap flights from Boston to Chicago O'Hare Intl Airport from $44

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to Chicago O'Hare Intl Airport departing on 2/19. 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 Boston to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Boston to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Boston to Chicago.

Cheap last minute flights

Planning a quick getaway from Boston to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Boston to Chicago

Find recent round-trip train or bus tickets from Boston to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
1:16 pm - 11:37 pmBOS-ORD
11h 21m1 stop
8:00 am - 12:16 amORD-BOS
15h 16m1 stop
$94Spirit Airlines
Find Deal
Tue, Oct 29 - Wed, Oct 30
3:15 pm - 7:22 pmBOS-ORD
5h 07m1 stop
6:07 am - 8:16 pmORD-BOS
13h 09m1 stop
$96Spirit Airlines
Find Deal
Sat, Jan 25 - Wed, Feb 5
11:05 am - 1:03 pmBOS-ORD
2h 58mnonstop
6:40 am - 10:00 amORD-BOS
2h 20mnonstop
$147Delta
Find Deal
Wed, Nov 20 - Wed, Dec 4
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
4:53 pm - 8:14 pmORD-BOS
2h 21mnonstop
$152JetBlue
Find Deal
Sun, Nov 17 - Wed, Nov 20
2:14 pm - 4:08 pmBOS-ORD
2h 54mnonstop
8:56 am - 6:36 pmORD-BOS
8h 40m1 stop
$156JetBlue
Find Deal
Tue, Nov 5 - Sat, Nov 9
6:00 am - 7:56 amBOS-ORD
2h 56mnonstop
7:30 am - 10:49 amORD-BOS
2h 19mnonstop
$157United Airlines
Find Deal
Fri, Dec 6 - Sun, Dec 8
5:45 am - 9:36 amBOS-ORD
4h 51m1 stop
9:15 pm - 12:44 amORD-BOS
2h 29mnonstop
$167United Airlines
Find Deal
Thu, Oct 17 - Fri, Oct 18
7:50 pm - 9:51 pmBOS-ORD
3h 01mnonstop
10:25 am - 1:55 pmORD-BOS
2h 30mnonstop
$172Delta
Find Deal
Fri, Nov 15 - Wed, Nov 20
12:02 pm - 5:45 pmBOS-ORD
6h 43m1 stop
8:10 am - 11:23 amORD-BOS
2h 13mnonstop
$202American Airlines
Find Deal
Sat, Nov 16 - Tue, Nov 19
12:02 pm - 5:45 pmBOS-ORD
6h 43m1 stop
8:10 am - 11:23 amORD-BOS
2h 13mnonstop
$207American Airlines
Find Deal
Sat, Nov 9 - Tue, Nov 12
3:15 pm - 7:22 pmBOS-ORD
5h 07m1 stop
$44Spirit Airlines
Find Deal
Wed, Feb 19
1:16 pm - 11:37 pmBOS-ORD
11h 21m1 stop
$45Spirit Airlines
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Wed, Oct 30
6:00 am - 7:56 amBOS-ORD
2h 56mnonstop
$74United Airlines
Find Deal
Sat, Dec 7
3:50 pm - 5:53 pmBOS-ORD
3h 03mnonstop
$79JetBlue
Find Deal
Thu, Jan 9
11:35 am - 5:17 pmBOS-ORD
6h 42m1 stop
$88JetBlue
Find Deal
Sat, Oct 19
12:11 pm - 2:25 pmBOS-ORD
3h 14mnonstop
$90American Airlines
Find Deal
Wed, Feb 19
2:40 pm - 4:49 pmBOS-ORD
3h 09mnonstop
$100Delta
Find Deal
Mon, Jan 6
6:00 am - 12:04 pmBOS-ORD
7h 04m1 stop
$123United Airlines
Find Deal
Mon, Oct 14
6:58 am - 10:44 amBOS-ORD
4h 46m1 stop
$128American Airlines
Find Deal
Fri, Nov 29
7:00 am - 1:05 pmBOS-ORD
7h 05m1 stop
$158Delta
Find Deal
Sun, Jan 5
10:50 am - 11:05 pmBOS-ORD
13h 15m1 stop
1:39 pm - 12:28 amORD-BOS
9h 49m1 stop
Tue, Oct 8 - Sat, Oct 12
6:00 am - 3:40 pmBOS-ORD
10h 40m1 stop
1:39 pm - 12:28 amORD-BOS
9h 49m1 stop
$204Frontier
Find Deal
Thu, Oct 10 - Sat, Oct 12
7:40 pm - 9:32 pmBOS-ORD
2h 52mnonstop
6:23 am - 9:47 amORD-BOS
2h 24mnonstop
$242Delta
Find Deal
Sat, Oct 12 - Wed, Oct 16
5:44 am - 10:40 amBOS-ORD
5h 56m1 stop
6:23 am - 9:47 amORD-BOS
2h 24mnonstop
$252Delta
Find Deal
Sat, Oct 12 - Sun, Oct 13
7:15 pm - 11:14 pmBOS-ORD
4h 59m1 stop
10:45 am - 4:40 pmORD-BOS
4h 55m1 stop
$261United Airlines
Find Deal
Sat, Oct 12 - Sun, Oct 13
6:03 am - 10:19 amBOS-ORD
5h 16m1 stop
7:00 am - 10:27 amORD-BOS
2h 27mnonstop
$262American Airlines
Find Deal
Sat, Oct 12 - Sun, Oct 13
11:20 am - 1:03 pmBOS-ORD
2h 43mnonstop
7:30 am - 10:56 amORD-BOS
2h 26mnonstop
$294United Airlines
Find Deal
Thu, Oct 10 - Sun, Oct 13
11:35 am - 5:17 pmBOS-ORD
6h 42m1 stop
6:15 pm - 12:21 amORD-BOS
5h 06m1 stop
$296JetBlue
Find Deal
Wed, Oct 9 - Wed, Oct 16
6:30 am - 10:23 amBOS-ORD
4h 53m1 stop
6:30 am - 12:33 pmORD-BOS
5h 03m1 stop
$301American Airlines
Find Deal
Thu, Oct 10 - Sun, Oct 13
11:45 am - 5:17 pmBOS-ORD
6h 32m1 stop
9:25 am - 5:55 pmORD-BOS
7h 30m1 stop
$321JetBlue
Find Deal
Tue, Oct 8 - Wed, Oct 16
7:40 am - 9:50 amBOS-ORD
3h 10mnonstop
7:50 pm - 11:08 pmORD-BOS
2h 18mnonstop
$103Spirit Airlines
Find Deal
Tue, Nov 12 - Thu, Nov 14
11:35 am - 1:27 pmBOS-ORD
2h 52mnonstop
7:50 pm - 11:08 pmORD-BOS
2h 18mnonstop
$108Spirit Airlines
Find Deal
Sat, Nov 2 - Thu, Nov 7
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
9:56 am - 1:14 pmORD-BOS
2h 18mnonstop
$147JetBlue
Find Deal
Tue, Nov 12 - Sat, Nov 16
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
4:53 pm - 8:14 pmORD-BOS
2h 21mnonstop
$152JetBlue
Find Deal
Sun, Nov 17 - Wed, Nov 20
7:15 am - 9:10 amBOS-ORD
2h 55mnonstop
5:55 pm - 9:23 pmORD-BOS
2h 28mnonstop
$157Delta
Find Deal
Wed, Oct 16 - Sat, Nov 2
5:15 am - 7:17 amBOS-ORD
3h 02mnonstop
12:30 pm - 3:49 pmORD-BOS
2h 19mnonstop
$168American Airlines
Find Deal
Mon, Nov 25 - Wed, Dec 4
7:50 pm - 9:51 pmBOS-ORD
3h 01mnonstop
6:40 am - 10:00 amORD-BOS
2h 20mnonstop
$172Delta
Find Deal
Fri, Nov 15 - Wed, Nov 20
2:41 pm - 4:41 pmBOS-ORD
3h 00mnonstop
8:09 am - 11:22 amORD-BOS
2h 13mnonstop
$179American Airlines
Find Deal
Mon, Nov 25 - Tue, Dec 3
6:00 am - 7:48 amBOS-ORD
2h 48mnonstop
7:30 am - 10:56 amORD-BOS
2h 26mnonstop
$184United Airlines
Find Deal
Fri, Oct 18 - Sun, Oct 20
4:53 pm - 6:40 pmBOS-ORD
2h 47mnonstop
7:22 am - 10:41 amORD-BOS
2h 19mnonstop
$195United Airlines
Find Deal
Wed, Oct 23 - Sun, Oct 27

Frontier flights from Boston to Chicago O'Hare Intl Airport

Our best Frontier deals on Boston to Chicago O'Hare Intl Airport flight tickets
Frontier
Oct 30
BOS12:27 pmBoston Logan Intl
6h 10m
1 stop
ORD5:37 pmChicago O'Hare Intl
Nov 2
ORD1:39 pmChicago O'Hare Intl
9h 49m
1 stop
BOS12:28 amBoston Logan Intl
Frontier
Oct 22
BOS12:27 pmBoston Logan Intl
8h 15m
1 stop
ORD7:42 pmChicago O'Hare Intl
Nov 2
ORD1:39 pmChicago O'Hare Intl
9h 49m
1 stop
BOS12:28 amBoston Logan Intl
Frontier
Oct 22
BOS12:27 pmBoston Logan Intl
8h 15m
1 stop
ORD7:42 pmChicago O'Hare Intl
Nov 1
ORD10:37 pmChicago O'Hare Intl
10h 13m
1 stop
BOS9:50 amBoston Logan Intl

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

Our best Spirit Airlines deals on Boston to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Oct 29
BOS1:16 pmBoston Logan Intl
11h 21m
1 stop
ORD11:37 pmChicago O'Hare Intl
Oct 30
ORD8:00 amChicago O'Hare Intl
15h 16m
1 stop
BOS12:16 amBoston Logan Intl
Spirit Airlines
Jan 25
BOS3:15 pmBoston Logan Intl
5h 07m
1 stop
ORD7:22 pmChicago O'Hare Intl
Feb 5
ORD6:07 amChicago O'Hare Intl
13h 09m
1 stop
BOS8:16 pmBoston Logan Intl
Spirit Airlines
Oct 17
BOS11:35 amBoston Logan Intl
2h 52m
ORD1:27 pmChicago O'Hare Intl
Oct 19
ORD2:17 pmChicago O'Hare Intl
2h 25m
BOS5:42 pmBoston Logan Intl

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

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 from Boston to Chicago O'Hare Intl Airport?

September. The cheapest time of year to fly to Chicago O'Hare Intl Airport from Boston is September. Most expensive is November

What is the cheapest day to depart Boston for Chicago O'Hare Intl Airport?

Saturday. The cheapest day of the week is typically Saturday. The most expensive is typically Sunday

When is the cheapest time to fly from Boston to Chicago O'Hare Intl Airport?

In the evening. Boston to Chicago O'Hare Intl Airport flights are approximately 15% more expensive in the afternoon than in the evening

What is the cheapest airline that flies to Chicago O'Hare Intl Airport from Boston?

Spirit Airlines. Spirit Airlines, Frontier, and JetBlue are the most popular carriers operating from Boston to Chicago O'Hare Intl Airport

How far in advance should you book Boston to Chicago O'Hare Intl Airport flights?

57 days before. The cheapest time to buy a flight from Boston to Chicago O'Hare Intl Airport is approximately 57 days to departure

How many flights depart from Boston to Chicago O'Hare Intl Airport on average per day?

The number of flights available between Boston and Chicago O'Hare Intl Airport is 48 per day as of October 2024. The most frequent departure time is 3:00PM, with 50% of daily flights leaving in the afternoon.

How many flights depart from Boston to Chicago O'Hare Intl Airport on average per week?

As of October 2024, there are 337 flights per week flying from Boston to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Monday, with 20% of flights taking off on this day.

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

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

Can stopping save me money on Boston to Chicago O'Hare Intl Airport flights?

You could potentially save up to 18% on your flight if you consider stops on a Boston to Chicago O'Hare Intl Airport flight.

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

As of October 2024, prices for Boston to Chicago O'Hare Intl Airport flights are approximately 29% cheaper when compared to flights at the same time last year.

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

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

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

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

Best Price Found

$44

Fastest flight time

2h 48m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Boston in the past 72 hours is $44. The best round-trip flight deal from Boston to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $94.
The fastest flight from Boston to Chicago O'Hare Intl Airport takes 2h 48m
Direct flights go from Boston to Chicago O'Hare Intl Airport every day.

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

    A flight from Boston Logan Intl to Chicago O'Hare Intl will travel around 861.0 mi. 2h 48m is a normal flight duration for this route.

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Boston Logan Intl Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare 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 Chicago O'Hare 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 Boston to Chicago O'Hare Intl Airport?

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


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

Compare and see reviews for airlines that fly from Boston to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $39Free CancellationRating
6.3
8,221 reviews
Search Spirit Airlines flights
JetBluePriceFrom $84Free CancellationRating
7.5
3,602 reviews
Search JetBlue flights
FrontierPriceFrom $90Free CancellationRating
6.1
3,651 reviews
Search Frontier flights
DeltaPriceFrom $99Free CancellationRating
8.0
8,974 reviews
Search Delta flights
American AirlinesPriceFrom $135Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $151Free CancellationRating
7.4
9,373 reviews
Search United Airlines flights
  • Delta Flights From Boston to Chicago O'Hare Intl Airport

    Delta is one of the most popular airlines flying from Boston to Chicago O'Hare Intl Airport, operating 8 flights/week on average for this route. A good Delta flight deal for Boston to Chicago O'Hare Intl Airport starts from $99 round-trip, up to an average price of $264. Our users have rated Delta at 8.0/10.

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

    JetBlue (7.5/10 from 3,602 reviews) operates around 12 flights from Boston to Chicago O'Hare Intl Airport in any given week. The average JetBlue airfare for this route is around $233, with deals from around $84 rare but found on momondo. Referenced prices are for round-trip Boston to Chicago O'Hare Intl Airport flight searches in the last 72 hours.


Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Boston to Chicago for you.

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

Yes. momondo allows you to filter the results for Boston to Chicago flights to just show those with flexible booking policies.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Boston to Chicago.

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

Yes. momondo can track prices for Boston to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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