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Cheap flights from Chicago 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 to Boston departing on 7/29. 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

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Cheap round-trip flights

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
$112Spirit Airlines
Find Deal
Tue, Jul 29 - Tue, Jul 29
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
$125Spirit Airlines
Find Deal
Tue, Jul 29 - Tue, Aug 5
Delta Logo
7:20 pm - 10:58 pmORD-BOS
2h 38mnonstop
Delta Logo
7:20 am - 9:15 amBOS-ORD
2h 55mnonstop
$137Delta
Find Deal
Fri, Aug 15 - Sat, Aug 23
Southwest Logo
5:40 pm - 9:00 pmMDW-BOS
2h 20mnonstop
Southwest Logo
5:40 pm - 7:20 pmBOS-MDW
2h 40mnonstop
$137Southwest
Find Deal
Sat, Aug 16 - Wed, Aug 20
American Airlines Logo
6:05 am - 9:32 amORD-BOS
2h 27mnonstop
American Airlines Logo
7:01 am - 9:05 amBOS-ORD
3h 04mnonstop
$139American Airlines
Find Deal
Sat, Sep 27 - Mon, Sep 29
American Airlines Logo
8:15 am - 11:36 amORD-BOS
2h 21mnonstop
American Airlines Logo
5:28 am - 7:24 amBOS-ORD
2h 56mnonstop
$140American Airlines
Find Deal
Tue, Jul 15 - Fri, Aug 15
United Airlines Logo
7:30 am - 10:57 amORD-BOS
2h 27mnonstop
United Airlines Logo
7:04 pm - 11:41 pmBOS-ORD
5h 37m1 stop
$143United Airlines
Find Deal
Tue, Aug 5 - Tue, Aug 12
Southwest Logo
5:40 pm - 9:00 pmMDW-BOS
2h 20mnonstop
Southwest Logo
11:25 am - 3:20 pmBOS-MDW
4h 55m1 stop
$147Southwest
Find Deal
Sat, Aug 16 - Wed, Aug 20
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
United Airlines Logo
6:00 am - 7:57 amBOS-ORD
2h 57mnonstop
$150United Airlines
Find Deal
Sat, Oct 11 - Sun, Oct 12
Delta Logo
7:00 am - 10:29 amORD-BOS
2h 29mnonstop
Delta Logo
2:55 pm - 4:50 pmBOS-ORD
2h 55mnonstop
$155Delta
Find Deal
Sat, Aug 23 - Tue, Aug 26

Spirit Airlines flights from Chicago to Boston

Our best Spirit Airlines deals on Chicago to Boston flight tickets
Spirit Airlines
Jul 29
ORD5:05 amChicago O'Hare Intl
13h 29m
1 stop
BOS7:34 pmBoston Logan Intl
Jul 29
BOS8:39 pmBoston Logan Intl
13h 16m
1 stop
ORD8:55 amChicago O'Hare Intl
Spirit Airlines
Jul 29
ORD5:05 amChicago O'Hare Intl
13h 29m
1 stop
BOS7:34 pmBoston Logan Intl
Aug 5
BOS8:39 pmBoston Logan Intl
13h 16m
1 stop
ORD8:55 amChicago O'Hare Intl
Spirit Airlines
Jul 29
ORD10:00 amChicago O'Hare Intl
8h 30m
1 stop
BOS7:30 pmBoston Logan Intl
Aug 5
BOS8:39 pmBoston Logan Intl
13h 16m
1 stop
ORD8:55 amChicago O'Hare Intl

Delta flights from Chicago to Boston

Our best Delta deals on Chicago to Boston flight tickets
Delta
Aug 15
ORD7:20 pmChicago O'Hare Intl
2h 38m
BOS10:58 pmBoston Logan Intl
Aug 23
BOS7:20 amBoston Logan Intl
2h 55m
ORD9:15 amChicago O'Hare Intl
Delta
Aug 23
ORD7:00 amChicago O'Hare Intl
2h 29m
BOS10:29 amBoston Logan Intl
Aug 26
BOS2:55 pmBoston Logan Intl
2h 55m
ORD4:50 pmChicago O'Hare Intl
Delta
Jul 28
ORD7:00 amChicago O'Hare Intl
2h 31m
BOS10:31 amBoston Logan Intl
Aug 5
BOS7:20 amBoston Logan Intl
2h 58m
ORD9:18 amChicago O'Hare Intl

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, August 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 $187. If you aren’t able to travel during the month of August, then book flights to Boston from Chicago during September instead. Flights to Boston in September, while not as cheap as those in August, still average around $187.

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

The cheapest day to depart from Chicago to Boston is on a Saturday when prices can be found for as low as $235. 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 $303.

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 $208. 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 $280 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 $230 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 $194 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 July 2025, prices for Chicago to Boston flights are approximately 49% 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

$55

Fastest flight time

2h 15m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

Airports in Boston

1 airport
The best one-way flight to Boston from Chicago in the past 72 hours is $55. The best round-trip flight deal from Chicago to Boston found on momondo in the last 72 hours is $112.
The fastest flight from Chicago to Boston takes 2h 15m
Direct flights go from Chicago to Boston on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines, Southwest and American Airlines.
There is 1 airport near Boston: Boston Logan Intl (BOS)

  • 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 $36Free CancellationRating
6.3
8,086 reviews
Search Spirit Airlines flights
JetBluePriceFrom $78Free CancellationRating
7.3
2,916 reviews
Search JetBlue flights
DeltaPriceFrom $90Free CancellationRating
8.0
7,982 reviews
Search Delta flights
FrontierPriceFrom $100Free CancellationRating
5.9
3,286 reviews
Search Frontier flights
American AirlinesPriceFrom $125Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $130Free CancellationRating
7.4
8,861 reviews
Search United Airlines flights
SouthwestPriceFrom $153Free CancellationRating
8.0
4,266 reviews
Search Southwest flights
  • Delta Flights From Chicago to Boston

    Delta flight deals from Chicago to Boston start from $90 round-trip. Over the 8 Delta flights for this route in a normal week, average airfare is usually $222 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 (8.0/10, 4,270 ratings). Southwest flies from Chicago to Boston around 24 times per week, with deals starting from $153 round-trip and rising to an average price of around $276.


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
Nashua
Cambridge
Laconia
Kennebunkport
Narragansett
Brockton
Concord
Everett
Gloucester
South Yarmouth
Wells
Warwick
Revere

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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1 adult
Tue 7/8
Tue 7/15

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