Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Boston to Chicago O'Hare Intl Airport from $45

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 12/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

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.
10:34 am - 9:07 pmBOS-ORD
11h 33m1 stop
9:58 am - 12:38 amORD-BOS
13h 40m1 stop
$101Spirit Airlines
Find Deal
Fri, Dec 6 - Tue, Dec 10
8:54 am - 3:43 pmBOS-ORD
7h 49m1 stop
9:58 am - 12:38 amORD-BOS
13h 40m1 stop
Mon, Dec 9 - Tue, Dec 10
6:00 am - 8:05 amBOS-ORD
3h 05mnonstop
8:51 am - 12:13 pmORD-BOS
2h 22mnonstop
$157JetBlue
Find Deal
Thu, Dec 5 - Mon, Dec 9
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
10:14 am - 3:43 pmORD-BOS
4h 29m1 stop
$161JetBlue
Find Deal
Tue, Dec 10 - Tue, Dec 10
7:20 am - 9:29 amBOS-ORD
3h 09mnonstop
7:35 am - 11:03 amORD-BOS
2h 28mnonstop
$173Delta
Find Deal
Thu, Dec 5 - Wed, Dec 25
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
6:00 am - 12:07 pmORD-BOS
5h 07m1 stop
$183United Airlines
Find Deal
Wed, Jan 1 - Mon, Jan 20
10:45 am - 12:41 pmBOS-ORD
2h 56mnonstop
10:37 am - 2:02 pmORD-BOS
2h 25mnonstop
$189United Airlines
Find Deal
Tue, Dec 3 - Wed, Dec 4
9:00 am - 11:03 amBOS-ORD
3h 03mnonstop
7:35 am - 11:03 amORD-BOS
2h 28mnonstop
$194Delta
Find Deal
Tue, Dec 31 - Sun, Jan 5
5:15 am - 7:19 amBOS-ORD
3h 04mnonstop
12:30 pm - 3:49 pmORD-BOS
2h 19mnonstop
$202American Airlines
Find Deal
Sun, Jan 5 - Wed, Jan 8
7:00 am - 12:25 pmBOS-ORD
6h 25m1 stop
2:14 pm - 5:33 pmORD-BOS
2h 19mnonstop
$207American Airlines
Find Deal
Wed, Dec 4 - Sat, Dec 7
5:00 am - 4:06 pmBOS-ORD
12h 06m1 stop
$45Spirit Airlines
Find Deal
Tue, Dec 10
6:00 am - 11:47 amBOS-ORD
6h 47m1 stop
$53Frontier
Find Deal
Wed, Jan 8
7:20 am - 9:29 amBOS-ORD
3h 09mnonstop
$78Delta
Find Deal
Wed, Dec 4
3:52 pm - 5:55 pmBOS-ORD
3h 03mnonstop
$79JetBlue
Find Deal
Wed, Feb 5
7:25 am - 9:28 amBOS-ORD
3h 03mnonstop
$83Delta
Find Deal
Fri, Dec 6
11:28 am - 3:44 pmBOS-ORD
5h 16m1 stop
$88JetBlue
Find Deal
Sun, Jan 19
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
$95United Airlines
Find Deal
Tue, Dec 31
6:00 am - 7:56 amBOS-ORD
2h 56mnonstop
$124United Airlines
Find Deal
Tue, Nov 26
8:30 am - 10:32 amBOS-ORD
3h 02mnonstop
$125American Airlines
Find Deal
Wed, Nov 27
7:00 am - 11:13 amBOS-ORD
5h 13m1 stop
$133American Airlines
Find Deal
Wed, Nov 27
11:35 am - 12:28 amBOS-ORD
13h 53m1 stop
11:45 am - 12:38 amORD-BOS
11h 53m1 stop
Sat, Nov 23 - Fri, Dec 6
11:35 am - 12:28 amBOS-ORD
13h 53m1 stop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
Sat, Nov 23 - Thu, Nov 28
11:35 am - 12:28 amBOS-ORD
13h 53m1 stop
2:25 pm - 12:44 amORD-BOS
9h 19m1 stop
$139Frontier
Find Deal
Sat, Nov 23 - Wed, Nov 27
7:20 am - 9:29 amBOS-ORD
3h 09mnonstop
12:40 pm - 3:58 pmORD-BOS
2h 18mnonstop
$252Delta
Find Deal
Sun, Nov 24 - Sat, Dec 7
9:05 am - 12:50 pmBOS-ORD
4h 45m1 stop
7:15 am - 10:49 amORD-BOS
2h 34mnonstop
$262Delta
Find Deal
Sat, Nov 23 - Sat, Dec 7
1:59 pm - 3:53 pmBOS-ORD
2h 54mnonstop
8:50 am - 12:12 pmORD-BOS
2h 22mnonstop
$282JetBlue
Find Deal
Fri, Nov 22 - Wed, Dec 4
2:41 pm - 4:41 pmBOS-ORD
3h 00mnonstop
7:00 am - 10:19 amORD-BOS
2h 19mnonstop
$288American Airlines
Find Deal
Fri, Nov 22 - Tue, Nov 26
9:30 am - 11:27 amBOS-ORD
2h 57mnonstop
8:20 am - 11:42 amORD-BOS
2h 22mnonstop
$297JetBlue
Find Deal
Mon, Nov 25 - Fri, Nov 29
11:32 am - 3:43 pmBOS-ORD
5h 11m1 stop
11:59 pm - 3:18 amORD-BOS
2h 19mnonstop
$307United Airlines
Find Deal
Mon, Nov 25 - Sun, Dec 1
8:00 am - 12:25 pmBOS-ORD
5h 25m1 stop
8:10 am - 3:23 pmORD-BOS
6h 13m1 stop
$311American Airlines
Find Deal
Mon, Nov 25 - Sat, Nov 30
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
8:51 am - 12:13 pmORD-BOS
2h 22mnonstop
$157JetBlue
Find Deal
Fri, Dec 6 - Wed, Dec 11
11:05 am - 1:03 pmBOS-ORD
2h 58mnonstop
6:30 am - 10:00 amORD-BOS
2h 30mnonstop
$158Delta
Find Deal
Thu, Dec 5 - Mon, Dec 9
11:05 am - 1:00 pmBOS-ORD
2h 55mnonstop
6:30 am - 10:00 amORD-BOS
2h 30mnonstop
$165Delta
Find Deal
Thu, Dec 12 - Fri, Dec 13
1:59 pm - 3:53 pmBOS-ORD
2h 54mnonstop
8:50 am - 12:12 pmORD-BOS
2h 22mnonstop
$167JetBlue
Find Deal
Tue, Dec 3 - Thu, Dec 5
10:45 am - 12:41 pmBOS-ORD
2h 56mnonstop
9:20 am - 12:45 pmORD-BOS
2h 25mnonstop
$184United Airlines
Find Deal
Tue, Dec 3 - Thu, Dec 5
12:12 pm - 2:10 pmBOS-ORD
2h 58mnonstop
7:30 am - 10:56 amORD-BOS
2h 26mnonstop
$185United Airlines
Find Deal
Thu, Jan 16 - Mon, Jan 20
6:45 am - 8:49 amBOS-ORD
3h 04mnonstop
8:30 pm - 12:15 amORD-BOS
2h 45mnonstop
$194American Airlines
Find Deal
Tue, Dec 31 - Sun, Jan 5
5:15 am - 7:19 amBOS-ORD
3h 04mnonstop
12:30 pm - 3:49 pmORD-BOS
2h 19mnonstop
$202American Airlines
Find Deal
Sun, Jan 5 - Wed, Jan 8
5:30 am - 7:37 amBOS-ORD
3h 07mnonstop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
$425Spirit Airlines
Find Deal
Sat, Nov 30 - Mon, Dec 2
5:30 am - 7:37 amBOS-ORD
3h 07mnonstop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
$433Spirit Airlines
Find Deal
Sat, Nov 30 - Mon, Dec 2

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
Jan 8
BOS6:00 amBoston Logan Intl
6h 47m
1 stop
ORD11:47 amChicago O'Hare Intl
Jan 16
ORD4:41 pmChicago O'Hare Intl
6h 58m
1 stop
BOS12:39 amBoston Logan Intl
Frontier
Dec 17
BOS5:45 amBoston Logan Intl
11h 48m
1 stop
ORD4:33 pmChicago O'Hare Intl
Jan 6
ORD4:28 pmChicago O'Hare Intl
7h 13m
1 stop
BOS12:41 amBoston Logan Intl
Frontier
Jan 6
BOS11:55 amBoston Logan Intl
12h 02m
1 stop
ORD10:57 pmChicago O'Hare Intl
Jan 9
ORD5:02 pmChicago O'Hare Intl
6h 28m
1 stop
BOS12:30 amBoston Logan Intl

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

Our best American Airlines deals on Boston to Chicago O'Hare Intl Airport flight tickets
American Airlines
Dec 3
BOS12:00 pmBoston Logan Intl
2h 59m
ORD1:59 pmChicago O'Hare Intl
Dec 8
ORD8:35 pmChicago O'Hare Intl
2h 35m
BOS12:10 amBoston Logan Intl
American Airlines
Jan 5
BOS5:15 amBoston Logan Intl
3h 04m
ORD7:19 amChicago O'Hare Intl
Jan 8
ORD12:30 pmChicago O'Hare Intl
2h 19m
BOS3:49 pmBoston Logan Intl
American Airlines
Dec 4
BOS7:00 amBoston Logan Intl
6h 25m
1 stop
ORD12:25 pmChicago O'Hare Intl
Dec 7
ORD2:14 pmChicago O'Hare Intl
2h 19m
BOS5:33 pmBoston Logan Intl

See travel insights to Chicago from

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?

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

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

Wednesday. The cheapest day of the week is typically Wednesday. 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 13% more expensive in the afternoon than in the evening

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

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 37% 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 November 2024, prices for Boston to Chicago O'Hare Intl Airport flights are approximately 16% 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

$45

Fastest flight time

2h 47m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Boston in the past 72 hours is $45. The best round-trip flight deal from Boston to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $101.
The fastest flight from Boston to Chicago O'Hare Intl Airport takes 2h 47m
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 54m 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
8,174 reviews
Search Spirit Airlines flights
JetBluePriceFrom $83Free CancellationRating
7.4
3,394 reviews
Search JetBlue flights
DeltaPriceFrom $94Free CancellationRating
8.0
8,756 reviews
Search Delta flights
FrontierPriceFrom $98Free CancellationRating
6.1
3,539 reviews
Search Frontier flights
American AirlinesPriceFrom $135Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $149Free CancellationRating
7.4
9,171 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 22 flights/week on average for this route. A good Delta flight deal for Boston to Chicago O'Hare Intl Airport starts from $94 round-trip, up to an average price of $252. Our users have rated Delta at 8.0/10.

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

    JetBlue (7.4/10 from 3,394 reviews) operates around 4 flights from Boston to Chicago O'Hare Intl Airport in any given week. The average JetBlue airfare for this route is around $234, with deals from around $83 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.


An easier way to manage your Chicago O'Hare Intl Airport 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Mon 11/25
Mon 12/2
Email me momondo's favorite deals

Find better results for your trip to Chicago