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Cheap flights from Chicago to Boston from $67

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 11/18. 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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0 bags

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Delta Logo
7:10 am - 10:35 amORD-BOS
2h 25mnonstop
Delta Logo
7:52 pm - 9:47 pmBOS-ORD
2h 55mnonstop
$127Delta
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Thu, Nov 20 - Fri, Dec 5
Southwest Logo
2:55 pm - 11:15 pmMDW-BOS
7h 20m1 stop
Southwest Logo
5:30 am - 7:15 amBOS-MDW
2h 45mnonstop
$127Southwest
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Fri, Nov 7 - Tue, Nov 11
United Airlines Logo
9:20 am - 12:44 pmORD-BOS
2h 24mnonstop
United Airlines Logo
7:30 am - 9:30 amBOS-ORD
3h 00mnonstop
$133United Airlines
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Sun, Nov 9 - Sun, Nov 16
United Airlines Logo
6:15 am - 9:30 amORD-BOS
2h 15mnonstop
United Airlines Logo
6:00 am - 8:00 amBOS-ORD
3h 00mnonstop
$135United Airlines
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Sun, Oct 26 - Fri, Oct 31
JetBlue Logo
11:20 am - 2:44 pmORD-BOS
2h 24mnonstop
JetBlue Logo
8:30 am - 10:35 amBOS-ORD
3h 05mnonstop
$138JetBlue
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Thu, Nov 6 - Sun, Nov 9
JetBlue Logo
11:20 am - 2:44 pmORD-BOS
2h 24mnonstop
JetBlue Logo
8:30 am - 10:35 amBOS-ORD
3h 05mnonstop
$141JetBlue
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Thu, Nov 6 - Sun, Nov 9
American Airlines Logo
1:04 pm - 4:32 pmORD-BOS
2h 28mnonstop
American Airlines Logo
7:00 am - 9:32 amBOS-ORD
3h 32mnonstop
$142American Airlines
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Tue, Dec 2 - Thu, Dec 4
American Airlines Logo
6:05 am - 9:32 amORD-BOS
2h 27mnonstop
American Airlines Logo
6:47 am - 8:45 amBOS-ORD
2h 58mnonstop
$145American Airlines
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Sun, Oct 26 - Wed, Oct 29
Spirit Airlines Logo
1:26 pm - 7:16 pmORD-BOS
28h 50m1 stop
Spirit Airlines Logo
6:16 am - 12:27 amBOS-ORD
19h 11m1 stop
$159Spirit Airlines
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Thu, Oct 30 - Tue, Nov 4
Spirit Airlines Logo
3:43 pm - 11:53 pmORD-BOS
7h 10m1 stop
Spirit Airlines Logo
11:13 am - 9:23 pmBOS-ORD
11h 10m1 stop
$166Spirit Airlines
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Tue, Dec 2 - Thu, Dec 4

United Airlines flights from Chicago to Boston

Our best United Airlines deals on Chicago to Boston flight tickets
United Airlines
Nov 9
ORD9:20 amChicago O'Hare Intl
2h 24m
BOS12:44 pmBoston Logan Intl
Nov 16
BOS7:30 amBoston Logan Intl
3h 00m
ORD9:30 amChicago O'Hare Intl
$133
Find similar
United Airlines
Oct 26
ORD6:15 amChicago O'Hare Intl
2h 15m
BOS9:30 amBoston Logan Intl
Oct 31
BOS6:00 amBoston Logan Intl
3h 00m
ORD8:00 amChicago O'Hare Intl
$135
Find similar
United Airlines
Nov 7
ORD7:15 amChicago O'Hare Intl
2h 19m
BOS10:34 amBoston Logan Intl
Nov 9
BOS6:00 amBoston Logan Intl
3h 00m
ORD8:00 amChicago O'Hare Intl
$136
Find similar

JetBlue flights from Chicago to Boston

Our best JetBlue deals on Chicago to Boston flight tickets
JetBlue
Nov 6
ORD11:20 amChicago O'Hare Intl
2h 24m
BOS2:44 pmBoston Logan Intl
Nov 9
BOS8:30 amBoston Logan Intl
3h 05m
ORD10:35 amChicago O'Hare Intl
$138
Find similar
JetBlue
Oct 23
ORD10:08 amChicago O'Hare Intl
2h 29m
BOS1:37 pmBoston Logan Intl
Nov 5
BOS8:30 amBoston Logan Intl
3h 05m
ORD10:35 amChicago O'Hare Intl
$139
Find similar
JetBlue
Nov 6
ORD11:20 amChicago O'Hare Intl
2h 24m
BOS2:44 pmBoston Logan Intl
Nov 9
BOS8:30 amBoston Logan Intl
3h 05m
ORD10:35 amChicago O'Hare Intl
$141
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 October 14, 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

Thu 11/20

7:10 am-10:35 am

Nonstop2h 25m

Boston Logan Intl

Fri 12/5

7:52 pm-9:47 pm

Nonstop2h 55m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 11/7

2:55 pm-11:15 pm

1 stop7h 20m

Boston Logan Intl

Tue 11/11

5:30 am-7:15 am

Nonstop2h 45m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 11/9

9:20 am-12:44 pm

Nonstop2h 24m

Boston Logan Intl

Sun 11/16

7:30 am-9:30 am

Nonstop3h 00m

$133

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 10/26

6:15 am-9:30 am

Nonstop2h 15m

Boston Logan Intl

Fri 10/31

6:00 am-8:00 am

Nonstop3h 00m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 11/6

11:20 am-2:44 pm

Nonstop2h 24m

Boston Logan Intl

Sun 11/9

8:30 am-10:35 am

Nonstop3h 05m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 11/6

11:20 am-2:44 pm

Nonstop2h 24m

Boston Logan Intl

Sun 11/9

8:30 am-10:35 am

Nonstop3h 05m

$141

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/2

1:04 pm-4:32 pm

Nonstop2h 28m

Boston Logan Intl

Thu 12/4

7:00 am-9:32 am

Nonstop3h 32m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 10/26

6:05 am-9:32 am

Nonstop2h 27m

Boston Logan Intl

Wed 10/29

6:47 am-8:45 am

Nonstop2h 58m

$145

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 10/30

1:26 pm-7:16 pm

1 stop28h 50m

Boston Logan Intl

Tue 11/4

6:16 am-12:27 am

1 stop19h 11m

$159

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/2

3:43 pm-11:53 pm

1 stop7h 10m

Boston Logan Intl

Thu 12/4

11:13 am-9:23 pm

1 stop11h 10m

$166

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Chicago and Boston?

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 $217.

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

The cheapest day to depart from Chicago to Boston is on a Thursday when prices can be found for as low as $243. 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 $310.

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 $225. 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 $305 per ticket.

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

Fly from Chicago O'Hare Intl 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 $236 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 $188 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 October 2025, prices for Chicago to Boston flights are approximately 4% more expensive 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

$102

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 $102. The best round-trip flight deal from Chicago to Boston found on momondo in the last 72 hours is $167.
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 15m 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
Spirit AirlinesPriceFrom $58Free CancellationRating
6.3
8,096 reviews
Search Spirit Airlines flights
JetBluePriceFrom $79Free CancellationRating
7.2
2,905 reviews
Search JetBlue flights
DeltaPriceFrom $97Free CancellationRating
7.9
7,975 reviews
Search Delta flights
FrontierPriceFrom $104Free CancellationRating
5.8
3,135 reviews
Search Frontier flights
American AirlinesPriceFrom $118Free CancellationRating
7.2
11,042 reviews
Search American Airlines flights
United AirlinesPriceFrom $125Free CancellationRating
7.4
8,976 reviews
Search United Airlines flights
SouthwestPriceFrom $137Free CancellationRating
8.0
4,238 reviews
Search Southwest flights

  • Southwest Flights From Chicago to Boston

    Southwest flight deals from Chicago to Boston start from $137 round-trip. Over the 24 Southwest flights for this route in a normal week, average airfare is usually $253 round-trip - but some users have found much cheaper deals with momondo.

  • Delta Flights From Chicago to Boston

    Another popular option for Chicago to Boston flights is Delta (7.9/10, 7,975 ratings). Delta flies from Chicago to Boston around 15 times per week, with deals starting from $97 round-trip and rising to an average price of around $228.

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

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.

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