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 11/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Round-trip
1 adult
Economy
0 bags
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Thu 8/15
Thu 8/22
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Easily compare round-trip flights from Boston to Chicago
Below you can see the best fares for your round-trip flight route over the next six months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Boston to Chicago by changing tabs
Spirit Airlines
Sep 7
BOS11:35 amBoston Logan Intl
2h 52m
ORD1:27 pmChicago O'Hare Intl
Sep 14
ORD2:17 pmChicago O'Hare Intl
2h 25m
BOS5:42 pmBoston Logan Intl
$47
Find similarMultiple Airlines
Aug 26
BOS6:00 amBoston Logan Intl
6h 59m
1 stop
ORD11:59 amChicago O'Hare Intl
Aug 31
ORD8:59 pmChicago O'Hare Intl
2h 28m
BOS12:27 amBoston Logan Intl
$87
Find similarFrontier
Aug 17
BOS12:50 pmBoston Logan Intl
11h 59m
1 stop
MDW11:49 pmChicago Midway
Aug 24
MDW5:16 pmChicago Midway
6h 11m
1 stop
BOS12:27 amBoston Logan Intl
$100
Find similarSpirit Airlines
Nov 5
BOS5:30 amBoston Logan Intl
2h 52m
ORD7:22 amChicago O'Hare Intl
Nov 9
ORD8:59 pmChicago O'Hare Intl
2h 28m
BOS12:27 amBoston Logan Intl
$53
Find similarDelta
Sep 4
BOS5:05 pmBoston Logan Intl
3h 10m
ORD7:15 pmChicago O'Hare Intl
Sep 5
ORD6:35 amChicago O'Hare Intl
2h 26m
BOS10:01 amBoston Logan Intl
$117
Find similarSouthwest
Sep 1
BOS7:30 amBoston Logan Intl
2h 35m
MDW9:05 amChicago Midway
Sep 5
MDW6:10 pmChicago Midway
2h 15m
BOS9:25 pmBoston Logan Intl
$118
Find similarFind the cheapest one-way flights from Boston to Chicago
If you're looking for one-way flights from Boston to Chicago, view some of our deals below provided by Frontier, Southwest and Spirit Airlines
Spirit Airlines
Nov 20
BOS5:30 amBoston Logan Intl
2h 52m
ORD7:22 amChicago O'Hare Intl
$25
Find similarFrontier
Aug 19
BOS6:00 amBoston Logan Intl
6h 59m
1 stop
ORD11:59 amChicago O'Hare Intl
Spirit Airlines
Sep 7
BOS11:35 amBoston Logan Intl
2h 52m
ORD1:27 pmChicago O'Hare Intl
$29
Find similarFind the cheapest direct flights from Boston to Chicago
Spirit Airlines
Sep 7
BOS11:35 amBoston Logan Intl
2h 52m
ORD1:27 pmChicago O'Hare Intl
Sep 14
ORD2:17 pmChicago O'Hare Intl
2h 25m
BOS5:42 pmBoston Logan Intl
$47
Find similarSpirit Airlines
Nov 5
BOS5:30 amBoston Logan Intl
2h 52m
ORD7:22 amChicago O'Hare Intl
Nov 9
ORD8:59 pmChicago O'Hare Intl
2h 28m
BOS12:27 amBoston Logan Intl
$53
Find similarJetBlue
Sep 4
BOS8:15 amBoston Logan Intl
2h 53m
ORD10:08 amChicago O'Hare Intl
Sep 5
ORD8:20 pmChicago O'Hare Intl
2h 32m
BOS11:52 pmBoston Logan Intl
$117
Find similarSouthwest
Sep 1
BOS7:30 amBoston Logan Intl
2h 35m
MDW9:05 amChicago Midway
Sep 5
MDW6:10 pmChicago Midway
2h 15m
BOS9:25 pmBoston Logan Intl
$118
Find similarSpirit Airlines
Sep 7
BOS11:35 amBoston Logan Intl
2h 52m
ORD1:27 pmChicago O'Hare Intl
Sep 14
ORD2:17 pmChicago O'Hare Intl
2h 25m
BOS5:42 pmBoston Logan Intl
$55
Find similarDelta
Aug 28
BOS7:30 amBoston Logan Intl
3h 00m
ORD9:30 amChicago O'Hare Intl
Sep 1
ORD7:00 amChicago O'Hare Intl
2h 28m
BOS10:28 amBoston Logan Intl
$122
Find similarSearch last-minute flights to Chicago from Boston
Find and compare round-trip flight prices for your last-minute flight from Boston to Chicago
Spirit Airlines
Aug 20
BOS8:00 amBoston Logan Intl
2h 53m
ORD9:53 amChicago O'Hare Intl
Aug 24
ORD8:59 pmChicago O'Hare Intl
2h 28m
BOS12:27 amBoston Logan Intl
$70
Find similarMultiple Airlines
Aug 17
BOS6:00 amBoston Logan Intl
6h 00m
1 stop
ORD11:00 amChicago O'Hare Intl
Aug 24
ORD8:59 pmChicago O'Hare Intl
2h 28m
BOS12:27 amBoston Logan Intl
$88
Find similarFrontier
Aug 17
BOS12:50 pmBoston Logan Intl
11h 59m
1 stop
MDW11:49 pmChicago Midway
Aug 24
MDW5:16 pmChicago Midway
6h 11m
1 stop
BOS12:27 amBoston Logan Intl
$100
Find similarDelta
Aug 19
BOS7:40 pmBoston Logan Intl
2h 59m
ORD9:39 pmChicago O'Hare Intl
Aug 22
ORD1:59 pmChicago O'Hare Intl
2h 42m
BOS5:41 pmBoston Logan Intl
$126
Find similarJetBlue
Aug 16
BOS6:30 amBoston Logan Intl
2h 50m
ORD8:20 amChicago O'Hare Intl
Aug 17
ORD8:33 pmChicago O'Hare Intl
2h 26m
BOS11:59 pmBoston Logan Intl
Southwest
Aug 20
BOS3:25 pmBoston Logan Intl
2h 45m
MDW5:10 pmChicago Midway
Aug 21
MDW10:35 amChicago Midway
2h 20m
BOS1:55 pmBoston Logan Intl
$128
Find similarSpirit Airlines flights from Boston to Chicago
Our best Spirit Airlines deals on Boston to Chicago flight tickets
Spirit Airlines
Sep 7
BOS11:35 amBoston Logan Intl
2h 52m
ORD1:27 pmChicago O'Hare Intl
Sep 14
ORD2:17 pmChicago O'Hare Intl
2h 25m
BOS5:42 pmBoston Logan Intl
$47
Find similarSpirit Airlines
Nov 5
BOS5:30 amBoston Logan Intl
2h 52m
ORD7:22 amChicago O'Hare Intl
Nov 9
ORD8:59 pmChicago O'Hare Intl
2h 28m
BOS12:27 amBoston Logan Intl
$53
Find similarSpirit Airlines
Sep 7
BOS11:35 amBoston Logan Intl
2h 52m
ORD1:27 pmChicago O'Hare Intl
Sep 14
ORD2:17 pmChicago O'Hare Intl
2h 25m
BOS5:42 pmBoston Logan Intl
$55
Find similarUnited Airlines flights from Boston to Chicago
Our best United Airlines deals on Boston to Chicago flight tickets
United Airlines
Aug 16
BOS6:00 amBoston Logan Intl
2h 50m
ORD7:50 amChicago O'Hare Intl
Aug 18
ORD6:00 amChicago O'Hare Intl
2h 22m
BOS9:22 amBoston Logan Intl
$147
Find similarUnited Airlines
Aug 29
BOS10:10 amBoston Logan Intl
2h 43m
ORD11:53 amChicago O'Hare Intl
Sep 2
ORD6:05 amChicago O'Hare Intl
2h 26m
BOS9:31 amBoston Logan Intl
$167
Find similarHow 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 cheapest month to fly from Boston to Chicago?
January. The cheapest time of year to fly to Chicago from Boston is January. Most expensive is April
What is the cheapest day to depart Boston for Chicago?
Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Friday
When is the cheapest time to fly from Boston to Chicago?
In the evening. Boston to Chicago flights are approximately 20% more expensive at noon than in the evening
What is the cheapest airline that flies to Chicago from Boston?
Spirit Airlines. Spirit Airlines, Frontier, and Alaska Airlines are the most popular carriers operating from Boston to Chicago
What is the cheapest Boston to Chicago flight route?
Boston Logan Intl - Chicago O'Hare Intl. Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Boston - Chicago flight prices
How far in advance should you book Boston to Chicago flights?
23 days before. The cheapest time to buy a flight from Boston to Chicago is approximately 23 days to departure
How many flights depart from Boston to Chicago on average per day?
51 flights are operational weekly from Boston to Chicago as of August 2024. The most popular departure time for this route is 6:00AM, with 46% of flights per day taking off in the afternoon.
How many flights depart from Boston to Chicago on average per week?
As of August 2024, 363 flights take off from Boston and land in Chicago each week. The most common flight departure day for this route is Monday, with 18% of weekly flights taking off on this day.
What cabin class options are available on Boston to Chicago flights?
There are 4 cabin classes available to choose from on Boston to Chicago 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 flights?
No. A direct flight is the cheapest option for a flight between Boston to Chicago.
How have Boston to Chicago flight prices changed over time?
As of August 2024, prices for Boston to Chicago flights are approximately 23% cheaper when compared to flights at the same time last year.
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 | $25 |
|---|---|
Fastest flight time | 2h 30m |
Direct flights | Every day |
Airports in Chicago | 2 airports |
The best one-way flight to Chicago from Boston in the past 72 hours is $25. The best round-trip flight deal from Boston to Chicago found on momondo in the last 72 hours is $47.
The fastest flight from Boston to Chicago takes 2h 30m
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 30m 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 $47. 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 $209.
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 30m 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?
There are 7 operators available for flights from Boston Logan Intl Airport to Chicago as of August 2024.
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 circ*mstances. 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.
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 | ||
|---|---|---|---|---|---|
| Alaska Airlines | PriceFrom $39 | Free Cancellation | Rating 8.0 9,400 reviews | Search Alaska Airlines flights | |
| Spirit Airlines | PriceFrom $43 | Free Cancellation | Rating 6.3 8,344 reviews | Search Spirit Airlines flights | |
| JetBlue | PriceFrom $87 | Free Cancellation | Rating 7.5 3,892 reviews | Search JetBlue flights | |
| Frontier | PriceFrom $90 | Free Cancellation | Rating 6.2 3,795 reviews | Search Frontier flights | |
| Delta | PriceFrom $111 | Free Cancellation | Rating 8.0 9,497 reviews | Search Delta flights | |
| American Airlines | PriceFrom $138 | Free Cancellation | Rating 7.3 10,000 reviews | Search American Airlines flights | |
| United Airlines | PriceFrom $147 | Free Cancellation | Rating 7.4 9,935 reviews | Search United Airlines flights |
Alaska Airlines Flights From Boston to Chicago
The lowest priced Alaska Airlines flight from Boston to Chicago from the last 72 hours was $39. Generally, Alaska Airlines has 28 flights on this route every week with an average price of $159. Alaska Airlines is rated 8.0/10 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 $111 round-trip, depending on your selected dates, with average Delta deals seen on momondo around $365. Delta operates 28 flights to Chicago from Boston in an average week. Users have rated it 8.0/10 across 9,497 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 35m
$132 one-way$209 round-trip
Nonstop · from $209
Distance to downtown
ZUN • 0.7 mi
Boston to Chicago Buses
Trains
22h 15m
$108 one-way$216 round-trip
Nonstop · from $216
Distance to downtown
ZUN • 0.7 mi
Boston to Chicago Trains
Flights
2h 35m
$25 one-way$47 round-trip
Nonstop · from $471 stop · from $33
Distance to downtown
ORD • 15.9 mi
Boston to Chicago Flights
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Round-trip
1 adult
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To?
Thu 8/15
Thu 8/22
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Find better results for your trip to the United States
Fly into one of these airports located in ChicagoAirports listed have a maximum distance of 78.5 mi from Chicago
Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport
Fly your favorite airline to ChicagoAirlines are sorted and displayed according to clicks in the past 7 days on momondo
Airlines are sorted and displayed according to clicks in the past 7 days on momondo
American Airlines
Delta
United Airlines
Turkish Airlines
Lufthansa
Spirit Airlines
British Airways
Qatar Airways
Frontier
Ryanair
JetBlue
Air France
Popular cities in the United StatesPopular flights according to clicks in the last 7 days on momondo
Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $37
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Flights to Miamifrom $50
Flights to Las Vegasfrom $27
Flights to Orlandofrom $34
Flights to San Franciscofrom $38
Flights to Washington, D.C.from $33
Flights to Bostonfrom $42
Flights to Atlantafrom $36
Flights to Dallasfrom $25
Flights to Seattlefrom $35
Flights to Fort Lauderdalefrom $47
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According to popular flight searches on momondo this year
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