Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Boston from $62

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 to Boston departing on 1/28. 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

Discover deals from 900+ travel sites with momondo.

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.
Search flight deals

Find the cheapest flights from Chicago to Boston

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
7:45 am - 11:10 am
ORD
-
BOS
2h 25mnonstop
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
$124JetBlue
Sat, Jan 17 - Tue, Jan 20
United Airlines Logo
6:05 pm - 9:38 pm
ORD
-
BOS
2h 33mnonstop
United Airlines Logo
10:30 am - 12:34 pm
BOS
-
ORD
3h 04mnonstop
$127United Airlines
Sat, Jan 17 - Tue, Jan 20
Frontier Logo
5:01 pm - 1:13 am
MDW
-
BOS
7h 12m1 stop
Frontier Logo
6:00 am - 11:45 am
BOS
-
MDW
6h 45m1 stop
$128Frontier
Thu, Jan 22 - Thu, Jan 29
Multiple Airlines Logo
12:44 pm - 11:19 pm
ORD
-
BOS
9h 35m1 stop
Multiple Airlines Logo
6:00 am - 6:27 pm
BOS
-
ORD
13h 27m1 stop
$128Multiple Airlines
Sat, Jan 17 - Wed, Jan 21
Frontier Logo
2:42 pm - 1:13 am
ORD
-
BOS
9h 31m1 stop
Frontier Logo
6:00 am - 1:37 pm
BOS
-
ORD
8h 37m1 stop
$129Frontier
Thu, Jan 22 - Thu, Jan 29
Frontier Logo
5:01 pm - 1:13 am
MDW
-
BOS
7h 12m1 stop
Frontier Logo
6:00 am - 11:45 am
BOS
-
MDW
6h 45m1 stop
$129Frontier
Thu, Jan 22 - Thu, Jan 29
Southwest Logo
5:35 pm - 8:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
4:55 pm - 6:45 pm
BOS
-
MDW
2h 50mnonstop
$132Southwest
Wed, Jan 7 - Sat, Jan 17
Multiple Airlines Logo
6:05 am - 2:38 pm
ORD
-
BOS
7h 33m1 stop
Multiple Airlines Logo
6:00 am - 1:37 pm
BOS
-
ORD
8h 37m1 stop
$134Multiple Airlines
Wed, Jan 28 - Sun, Feb 1
American Airlines Logo
7:00 am - 10:28 am
ORD
-
BOS
2h 28mnonstop
American Airlines Logo
5:31 pm - 7:45 pm
BOS
-
ORD
3h 14mnonstop
$135American Airlines
Sat, Mar 7 - Mon, Mar 9
Southwest Logo
10:15 am - 1:30 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
$137Southwest
Sat, Jan 17 - Sun, Jan 18

United Airlines flights from Chicago to Boston

Our best United Airlines deals on Chicago to Boston flight tickets
United Airlines
Jan 17
ORD6:05 pmChicago O'Hare Intl
2h 33m
BOS9:38 pmBoston Logan Intl
Jan 20
BOS10:30 amBoston Logan Intl
3h 04m
ORD12:34 pmChicago O'Hare Intl
$127
Find similar
United Airlines
Dec 19
ORD7:45 amChicago O'Hare Intl
2h 22m
BOS11:07 amBoston Logan Intl
Jan 13
BOS12:45 pmBoston Logan Intl
3h 05m
ORD2:50 pmChicago O'Hare Intl
$142
Find similar
United Airlines
Jan 17
ORD6:05 pmChicago O'Hare Intl
2h 33m
BOS9:38 pmBoston Logan Intl
Jan 25
BOS7:07 pmBoston Logan Intl
5h 32m
1 stop
ORD11:39 pmChicago O'Hare Intl
$162
Find similar

Southwest flights from Chicago to Boston

Our best Southwest deals on Chicago to Boston flight tickets
Southwest
Jan 17
MDW10:15 amChicago Midway
2h 15m
BOS1:30 pmBoston Logan Intl
Jan 18
BOS5:30 amBoston Logan Intl
2h 50m
MDW7:20 amChicago Midway
$127
Find similar
Southwest
Jan 7
MDW5:35 pmChicago Midway
2h 15m
BOS8:50 pmBoston Logan Intl
Jan 17
BOS4:55 pmBoston Logan Intl
2h 50m
MDW6:45 pmChicago Midway
$132
Find similar
Southwest
Jan 17
MDW8:40 amChicago Midway
6h 30m
1 stop
BOS4:10 pmBoston Logan Intl
Jan 18
BOS5:30 amBoston Logan Intl
2h 50m
MDW7:20 amChicago Midway
$137
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 December 9, 2025.
Use the filters below to find and compare flights from Chicago to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/17

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Tue 1/20

3:35 pm-5:43 pm

Nonstop3h 08m

$124

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/17

6:05 pm-9:38 pm

Nonstop2h 33m

Boston Logan Intl

Tue 1/20

10:30 am-12:34 pm

Nonstop3h 04m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 1/22

5:01 pm-1:13 am

1 stop7h 12m

Boston Logan Intl

Thu 1/29

6:00 am-11:45 am

1 stop6h 45m

$128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/17

12:44 pm-11:19 pm

1 stop9h 35m

Boston Logan Intl

Wed 1/21

6:00 am-6:27 pm

1 stop13h 27m

$128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/22

2:42 pm-1:13 am

1 stop9h 31m

Boston Logan Intl

Thu 1/29

6:00 am-1:37 pm

1 stop8h 37m

$129

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 1/22

5:01 pm-1:13 am

1 stop7h 12m

Boston Logan Intl

Thu 1/29

6:00 am-11:45 am

1 stop6h 45m

$129

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 1/7

5:35 pm-8:50 pm

Nonstop2h 15m

Boston Logan Intl

Sat 1/17

4:55 pm-6:45 pm

Nonstop2h 50m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 1/28

6:05 am-2:38 pm

1 stop7h 33m

Boston Logan Intl

Sun 2/1

6:00 am-1:37 pm

1 stop8h 37m

$134

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 3/7

7:00 am-10:28 am

Nonstop2h 28m

Boston Logan Intl

Mon 3/9

5:31 pm-7:45 pm

Nonstop3h 14m

$135

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 1/17

10:15 am-1:30 pm

Nonstop2h 15m

Boston Logan Intl

Sun 1/18

5:30 am-7:20 am

Nonstop2h 50m

$137

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Boston from

How to get the cheapest flight ticket from Chicago 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 to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $207. If you aren’t able to travel during the month of September, then book flights to Boston from Chicago during January instead. Flights to Boston in January, while not as cheap as those in September, still average around $212.

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

The cheapest day to depart from Chicago to Boston is on a Wednesday when prices can be found for as low as $240. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Monday 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 to Boston in the evening for as low as $218. 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 $300 per ticket.

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

Fly from Chicago Midway to Boston Logan Intl for the best Chicago - 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 when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $231 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Chicago for as low as $183 on momondo.

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

There are 4 cabin classes available to choose from on Chicago 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 to Boston flight prices changed over time?

As of December 2025, prices for Chicago to Boston flights are approximately 21% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Boston

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

Cheap Chicago to Boston (CHI to BOS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Boston

Best Price Found

$98

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Boston

1 airport
The best one-way flight to Boston from Chicago in the past 72 hours is $98. The best round-trip flight deal from Chicago to Boston found on momondo in the last 72 hours is $127.
The fastest flight from Chicago to Boston takes 2h 15m
Direct flights go from Chicago to Boston every day.
There is 1 airport near Boston: Boston Logan Intl (BOS)
Search flight deals

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

    The distance between Chicago and Boston Logan Intl is about 847.9 mi. 2h 10m is a normal flight duration for this route.

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Boston Logan Intl Airport.

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

    The travel and health documents you'll need for your trip to Boston Logan Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Boston Logan Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Boston?

  • What is the most popular airline from Chicago to Boston?

Best airlines flying from Chicago to Boston

Compare and see reviews for airlines that fly from Chicago to Boston with momondo
Airline
Rating
Free Cancellation
Price
JetBluePriceFrom $78Free CancellationRating
7.2
2,899 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $83Free CancellationRating
6.3
8,171 reviews
Search Spirit Airlines flights
DeltaPriceFrom $104Free CancellationRating
7.9
8,010 reviews
Search Delta flights
FrontierPriceFrom $104Free CancellationRating
5.8
3,085 reviews
Search Frontier flights
American AirlinesPriceFrom $117Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights
United AirlinesPriceFrom $117Free CancellationRating
7.4
9,088 reviews
Search United Airlines flights
SouthwestPriceFrom $136Free CancellationRating
7.9
4,252 reviews
Search Southwest flights

  • Delta Flights From Chicago to Boston

    Delta flight deals from Chicago to Boston start from $104 round-trip. Over the 12 Delta flights for this route in a normal week, average airfare is usually $225 round-trip - but some users have found much cheaper deals with momondo.

  • Southwest Flights From Chicago to Boston

    Another popular option for Chicago to Boston flights is Southwest (7.9/10, 4,252 ratings). Southwest flies from Chicago to Boston around 8 times per week, with deals starting from $136 round-trip and rising to an average price of around $249.

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
South Yarmouth
Cambridge
Narragansett
Gloucester
Nashua
Falmouth
Laconia
Brockton
Concord
Everett
Sturbridge
Chatham

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Boston. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Chicago to Boston on momondo can be filtered to show those which offer flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Boston from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes. momondo can track prices for Chicago to Boston 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 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 1/8
Thu 1/15
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States