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Cheap flights from Boston to Chicago from $46

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 departing on 2/4. 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.
10:03 am - 11:58 pmBOS-ORD
14h 55m1 stop
5:45 am - 9:03 amORD-BOS
2h 18mnonstop
$97Spirit Airlines
Find Deal
mié., feb. 26 - mié., mar. 5
10:03 am - 10:03 pmBOS-ORD
13h 00m1 stop
5:45 am - 9:03 amORD-BOS
2h 18mnonstop
$100Spirit Airlines
Find Deal
mié., feb. 26 - mié., mar. 5
1:30 pm - 3:29 pmBOS-ORD
2h 59mnonstop
5:45 pm - 9:08 pmORD-BOS
2h 23mnonstop
$137JetBlue
Find Deal
mar., feb. 25 - mié., mar. 5
3:52 pm - 5:55 pmBOS-ORD
3h 03mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$147JetBlue
Find Deal
dom., feb. 2 - jue., feb. 6
5:15 am - 7:14 amBOS-ORD
2h 59mnonstop
12:33 pm - 3:49 pmORD-BOS
2h 16mnonstop
$158American Airlines
Find Deal
lun., mar. 31 - mié., abr. 2
4:43 pm - 6:41 pmBOS-ORD
2h 58mnonstop
6:30 pm - 9:59 pmORD-BOS
2h 29mnonstop
$192United Airlines
Find Deal
dom., ene. 19 - mar., ene. 21
9:26 am - 3:40 pmBOS-ORD
7h 14m1 stop
12:30 pm - 3:49 pmORD-BOS
2h 19mnonstop
$197American Airlines
Find Deal
sáb., feb. 1 - mié., feb. 5
10:52 am - 12:54 pmBOS-ORD
3h 02mnonstop
11:00 am - 2:23 pmORD-BOS
2h 23mnonstop
$199United Airlines
Find Deal
jue., feb. 13 - lun., feb. 17
7:15 am - 9:21 amBOS-ORD
3h 06mnonstop
7:10 am - 10:43 amORD-BOS
2h 33mnonstop
$218Delta
Find Deal
mié., feb. 19 - sáb., feb. 22
7:10 pm - 9:10 pmBOS-ORD
3h 00mnonstop
10:10 am - 3:53 pmORD-BOS
4h 43m1 stop
$237Delta
Find Deal
sáb., mar. 1 - sáb., mar. 8
11:31 am - 8:13 pmBOS-ORD
9h 42m1 stop
$46Spirit Airlines
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mar., feb. 4
6:00 am - 7:06 pmBOS-MDW
14h 06m1 stop
$47Frontier
Find Deal
mié., ene. 22
7:15 am - 9:25 amBOS-ORD
3h 10mnonstop
$68Delta
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mar., ene. 28
3:30 pm - 5:32 pmBOS-ORD
3h 02mnonstop
$69Delta
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mar., feb. 11
9:30 am - 11:28 amBOS-ORD
2h 58mnonstop
$79United Airlines
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dom., feb. 9
11:25 am - 3:43 pmBOS-ORD
5h 18m1 stop
$89JetBlue
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dom., feb. 9
11:20 am - 5:18 pmBOS-ORD
6h 58m1 stop
$99JetBlue
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jue., feb. 6
9:45 am - 2:47 pmBOS-ORD
6h 02m1 stop
$110United Airlines
Find Deal
mié., abr. 23
7:06 am - 11:53 amBOS-ORD
5h 47m1 stop
$133American Airlines
Find Deal
sáb., abr. 12
5:46 pm - 7:49 pmBOS-ORD
3h 03mnonstop
$219American Airlines
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sáb., feb. 15
6:00 am - 9:54 amBOS-ORD
28h 54m1 stop
1:45 pm - 12:39 amORD-BOS
9h 54m1 stop
$119Frontier
Find Deal
sáb., ene. 11 - mié., ene. 29
6:00 am - 9:54 amBOS-ORD
28h 54m1 stop
12:42 pm - 12:30 amORD-BOS
10h 48m1 stop
$121Frontier
Find Deal
sáb., ene. 11 - mié., ene. 15
6:00 am - 8:03 amBOS-ORD
3h 03mnonstop
10:35 am - 2:01 pmORD-BOS
2h 26mnonstop
$137United Airlines
Find Deal
lun., ene. 13 - jue., ene. 16
3:52 pm - 5:59 pmBOS-ORD
3h 07mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$138JetBlue
Find Deal
sáb., ene. 11 - lun., ene. 13
8:35 am - 3:44 pmBOS-ORD
8h 09m1 stop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$147JetBlue
Find Deal
lun., ene. 13 - mié., ene. 15
8:20 pm - 10:23 pmBOS-ORD
3h 03mnonstop
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
$155Delta
Find Deal
lun., ene. 13 - mié., ene. 15
12:12 pm - 2:08 pmBOS-ORD
2h 56mnonstop
12:51 pm - 6:26 pmORD-BOS
4h 35m1 stop
$157United Airlines
Find Deal
lun., ene. 13 - jue., ene. 16
5:45 pm - 7:52 pmBOS-ORD
3h 07mnonstop
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
$202Delta
Find Deal
sáb., ene. 11 - dom., ene. 19
3:40 pm - 7:24 pmBOS-ORD
4h 44m1 stop
8:05 am - 11:26 amORD-BOS
2h 21mnonstop
$203American Airlines
Find Deal
sáb., ene. 11 - lun., ene. 13
6:00 am - 8:08 amBOS-ORD
3h 08mnonstop
6:30 am - 10:03 amORD-BOS
2h 33mnonstop
$242American Airlines
Find Deal
dom., ene. 12 - jue., ene. 16
3:52 pm - 5:59 pmBOS-ORD
3h 07mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$136JetBlue
Find Deal
jue., ene. 23 - lun., ene. 27
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
9:00 am - 12:15 pmMDW-BOS
2h 15mnonstop
$137Southwest
Find Deal
jue., ene. 23 - sáb., ene. 25
1:30 pm - 3:29 pmBOS-ORD
2h 59mnonstop
5:45 pm - 9:08 pmORD-BOS
2h 23mnonstop
$137JetBlue
Find Deal
mar., feb. 25 - mié., mar. 5
3:30 pm - 5:36 pmBOS-ORD
3h 06mnonstop
10:40 am - 2:13 pmORD-BOS
2h 33mnonstop
$145Delta
Find Deal
mar., ene. 21 - jue., ene. 23
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
10:05 am - 1:20 pmMDW-BOS
2h 15mnonstop
$147Southwest
Find Deal
mié., ene. 29 - vie., ene. 31
8:20 pm - 10:19 pmBOS-ORD
2h 59mnonstop
7:10 am - 10:43 amORD-BOS
2h 33mnonstop
$157Delta
Find Deal
vie., feb. 7 - dom., feb. 9
5:15 am - 7:14 amBOS-ORD
2h 59mnonstop
12:33 pm - 3:49 pmORD-BOS
2h 16mnonstop
$158American Airlines
Find Deal
lun., mar. 31 - mié., abr. 2
6:00 am - 8:04 amBOS-ORD
3h 04mnonstop
4:00 pm - 7:20 pmORD-BOS
2h 20mnonstop
$165United Airlines
Find Deal
jue., mar. 6 - sáb., mar. 8
9:20 am - 11:22 amBOS-ORD
3h 02mnonstop
9:30 pm - 12:50 amORD-BOS
2h 20mnonstop
$166United Airlines
Find Deal
jue., mar. 20 - lun., mar. 24
8:55 pm - 10:53 pmBOS-ORD
2h 58mnonstop
6:35 pm - 10:05 pmORD-BOS
2h 30mnonstop
$179American Airlines
Find Deal
vie., abr. 4 - lun., abr. 7

Spirit Airlines flights from Boston to Chicago

Our best Spirit Airlines deals on Boston to Chicago flight tickets
Spirit Airlines
Feb 26
BOS10:03 amBoston Logan Intl
14h 55m
1 stop
ORD11:58 pmChicago O'Hare Intl
Mar 5
ORD5:45 amChicago O'Hare Intl
2h 18m
BOS9:03 amBoston Logan Intl
Spirit Airlines
Feb 26
BOS10:03 amBoston Logan Intl
13h 00m
1 stop
ORD10:03 pmChicago O'Hare Intl
Mar 5
ORD5:45 amChicago O'Hare Intl
2h 18m
BOS9:03 amBoston Logan Intl
Spirit Airlines
Feb 4
BOS11:31 amBoston Logan Intl
9h 42m
1 stop
ORD8:13 pmChicago O'Hare Intl
Feb 12
ORD3:14 pmChicago O'Hare Intl
7h 33m
1 stop
BOS11:47 pmBoston Logan Intl

JetBlue flights from Boston to Chicago

Our best JetBlue deals on Boston to Chicago flight tickets
JetBlue
Jan 23
BOS3:52 pmBoston Logan Intl
3h 07m
ORD5:59 pmChicago O'Hare Intl
Jan 27
ORD7:00 amChicago O'Hare Intl
2h 15m
BOS10:15 amBoston Logan Intl
JetBlue
Feb 25
BOS1:30 pmBoston Logan Intl
2h 59m
ORD3:29 pmChicago O'Hare Intl
Mar 5
ORD5:45 pmChicago O'Hare Intl
2h 23m
BOS9:08 pmBoston Logan Intl
JetBlue
Jan 11
BOS3:52 pmBoston Logan Intl
3h 07m
ORD5:59 pmChicago O'Hare Intl
Jan 13
ORD7:00 amChicago O'Hare Intl
2h 15m
BOS10:15 amBoston Logan Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Boston to Chicago

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 Boston and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Boston, with most prices found around $183. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Boston to Chicago during January average around $197.

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

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $222. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Boston to Chicago for around $278.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Boston to Chicago during this time can be as low as $237. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $277.

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

Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Boston Logan Intl - Chicago flight prices

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from Boston is 57 days out, which is when prices tend to be around $247. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $163.

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

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

How have Boston to Chicago flight prices changed over time?

As of January 2025, prices for Boston to Chicago flights are approximately 20% more expensive when compared to flights at the same time last year.

When to book flights from Boston to Chicago

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

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

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

Best Price Found

$46

Fastest flight time

2h 40m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Boston in the past 72 hours is $46. The best round-trip flight deal from Boston to Chicago found on momondo in the last 72 hours is $97.
The fastest flight from Boston to Chicago takes 2h 40m
Direct flights go from Boston to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • Is flying the fastest way to get from Boston to Chicago?

    To save time, the fastest way to travel is by flight from Boston to Chicago on Southwest. Expect the length of time you’ll spend onboard Southwest to be about 2h 40m compared to taking a train from Boston to Chicago or a bus from Boston to Chicago which have been found to be slower alternatives.

  • Is flying the cheapest way to get from Boston to Chicago?

    The cheapest way is to get a flight from Boston to Chicago, which can be as cheap as $97. A train from Boston to Chicago is more expensive than a flight, with prices starting at $216. A bus from Boston to Chicago is also an option, with an average price of $217.

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

    A flight from Boston Logan Intl to Chicago will travel around 847.9 mi. 2h 40m is a normal flight duration for this route.

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

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

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

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

    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.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

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


Best airlines flying from Boston to Chicago

Compare and see reviews for airlines that fly from Boston to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $39Free CancellationRating
6.3
8,074 reviews
Search Spirit Airlines flights
JetBluePriceFrom $80Free CancellationRating
7.4
3,191 reviews
Search JetBlue flights
DeltaPriceFrom $93Free CancellationRating
8.0
8,501 reviews
Search Delta flights
FrontierPriceFrom $98Free CancellationRating
6.0
3,428 reviews
Search Frontier flights
American AirlinesPriceFrom $138Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $147Free CancellationRating
7.4
8,941 reviews
Search United Airlines flights
SouthwestPriceFrom $148Free CancellationRating
8.1
4,649 reviews
Search Southwest flights
  • Southwest Flights From Boston to Chicago

    The lowest priced Southwest flight from Boston to Chicago from the last 72 hours was $148. Generally, Southwest has 10 flights on this route every week with an average price of $295. Southwest is rated 8.1/10 by our users.

  • Delta Flights From Boston to Chicago

    Delta is also a popular choice for this route. Delta flight deals for Boston to Chicago start from as low as $93 round-trip, depending on your selected dates, with average Delta deals seen on momondo around $345. Delta operates 21 flights to Chicago from Boston in an average week. Users have rated it 8.0/10 across 8,501 reviews.


Why use momondo?

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

It is quick and easy to find Boston to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

momondo does allow users to show only those flights to Chicago from Boston which offer a flexible booking policy as well as other useful filters and features.

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

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

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

Price alerts on flights to Chicago from Boston are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


Choose the best way to get from Boston to Chicago

Buses

27h 50m
$101 one-way$217 round-trip
Nonstop · from $217

Distance to downtown

G1N10.6 mi

Find Buses

Boston to Chicago Buses

Trains

22h 15m
$108 one-way$216 round-trip
Nonstop · from $216

Distance to downtown

ZUN0.7 mi

Flights

2h 40m
$46 one-way$97 round-trip
1 stop · from $97

Distance to downtown

ORD15.9 mi

An easier way to manage your Chicago trip

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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago