$91 Cheap Flights from Boston (BOS) to Chicago (CHI)
Popular airlines from Logan International Airport (BOS) to Chicago
JetBlue AirwaysJetBlue Airways
DeltaDelta
American AirlinesAmerican Airlines
UnitedUnited
Alaska AirlinesAlaska Airlines
Southwest AirlinesSouthwest Airlines
Frontier AirlinesFrontier Airlines
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Today's featured flight deals from Logan International Airport (BOS) to Chicago
Nonstop
Carry-on included
Lower price than typical
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Fri, Oct 9 at 10:00pm from Boston, arriving at 11:40pm in Chicago.Fri, Oct 9Returning on Mon, Oct 12 at 9:30pm from Chicago, arriving on Tue, Oct 13 at 9:35am in Boston.Mon, Oct 12
Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Fri, Oct 9 at 10:00pm from Boston, returning on Mon, Oct 12 at 9:30pm from Chicago priced at $6003-day tripfound 8 hours ago50% less than typical$600$600 - Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Fri, Oct 9 at 10:00pm from Boston, arriving at 11:40pm in Chicago.Fri, Oct 9Returning on Mon, Oct 12 at 10:05pm from Chicago, arriving on Tue, Oct 13 at 10:15am in Boston.Mon, Oct 12Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Fri, Oct 9 at 10:00pm from Boston, returning on Mon, Oct 12 at 10:05pm from Chicago priced at $6003-day tripfound 10 hours ago50% less than typical$600$600
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Fri, Oct 9 at 10:00pm from Boston, arriving at 11:40pm in Chicago.Fri, Oct 9Returning on Mon, Oct 12 at 10:05pm from Chicago, arriving on Tue, Oct 13 at 10:15am in Boston.Mon, Oct 12Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Fri, Oct 9 at 10:00pm from Boston, returning on Mon, Oct 12 at 10:05pm from Chicago priced at $6323-day tripfound 21 hours ago50% less than typical$632$632
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Fri, Oct 23 at 6:35pm from Boston, arriving at 8:10pm in Chicago.Fri, Oct 23Returning on Mon, Oct 26 at 6:45pm from Chicago, arriving at 10:05pm in Boston.Mon, Oct 26Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Fri, Oct 23 at 6:35pm from Boston, returning on Mon, Oct 26 at 6:45pm from Chicago priced at $2583-day tripfound 19 hours ago65% less than typical$258$258
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Thu, Oct 29 at 5:50am from Boston, arriving at 7:25am in Chicago.Thu, Oct 29Returning on Mon, Nov 2 at 7:50am from Chicago, arriving at 11:10am in Boston.Mon, Nov 2Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Thu, Oct 29 at 5:50am from Boston, returning on Mon, Nov 2 at 7:50am from Chicago priced at $2024-day tripfound 3 hours ago70% less than typical$202$202
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Thu, Nov 5 at 4:20pm from Boston, arriving at 6:05pm in Chicago.Thu, Nov 5Returning on Wed, Nov 11 at 8:30am from Chicago, arriving at 12:00pm in Boston.Wed, Nov 11Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Thu, Nov 5 at 4:20pm from Boston, returning on Wed, Nov 11 at 8:30am from Chicago priced at $2585-day tripfound 11 hours ago60% less than typical$258$258
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Thu, Nov 12 at 7:05am from Boston, arriving at 8:50am in Chicago.Thu, Nov 12Returning on Sun, Nov 15 at 8:00pm from Chicago, arriving at 11:31pm in Boston.Sun, Nov 15Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Thu, Nov 12 at 7:05am from Boston, returning on Sun, Nov 15 at 8:00pm from Chicago priced at $2583-day tripfound 20 hours ago30% less than typical$258$258
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Tue, Oct 20 at 4:20pm from Boston, arriving at 5:55pm in Chicago.Tue, Oct 20Returning on Fri, Oct 23 at 5:31pm from Chicago, arriving on Sat, Oct 24 at 12:20am in Boston.Fri, Oct 23Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Tue, Oct 20 at 4:20pm from Boston, returning on Fri, Oct 23 at 5:31pm from Chicago priced at $3253-day tripfound 18 hours ago25% less than typical$325$325
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Wed, Nov 11 at 5:55pm from Boston, arriving at 7:40pm in Chicago.Wed, Nov 11Returning on Mon, Nov 16 at 6:25pm from Chicago, arriving at 9:45pm in Boston.Mon, Nov 16Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Wed, Nov 11 at 5:55pm from Boston, returning on Mon, Nov 16 at 6:25pm from Chicago priced at $2025-day tripfound 4 hours ago45% less than typical$202$202
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Wed, Nov 11 at 5:55pm from Boston, arriving at 7:40pm in Chicago.Wed, Nov 11Returning on Mon, Nov 16 at 8:30am from Chicago, arriving at 12:00pm in Boston.Mon, Nov 16Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Wed, Nov 11 at 5:55pm from Boston, returning on Mon, Nov 16 at 8:30am from Chicago priced at $2024-day tripfound 18 hours ago45% less than typical$202$202
- Boston (BOS) to Chicago (ORD).Boston (BOS)Chicago (ORD)JetBlue Airways, nonstop.Departing on Sat, Oct 31 at 5:15pm from Boston, arriving at 7:29pm in Chicago.Sat, Oct 31Returning on Sun, Nov 8 at 7:50am from Chicago, arriving at 11:10am in Boston.Sun, Nov 8
JetBlue Airways•NonstopJetBlue AirwaysSelect JetBlue Airways flight departing on Sat, Oct 31 at 5:15pm from Boston, returning on Sun, Nov 8 at 7:50am from Chicago priced at $2587-day tripfound 1 hour ago25% less than typical$258$258 - Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Wed, Oct 28 at 7:20am from Boston, arriving at 8:55am in Chicago.Wed, Oct 28Returning on Sat, Oct 31 at 4:05pm from Chicago, arriving at 7:25pm in Boston.Sat, Oct 31Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Wed, Oct 28 at 7:20am from Boston, returning on Sat, Oct 31 at 4:05pm from Chicago priced at $2023-day tripfound 22 hours ago40% less than typical$202$202
- Boston (BOS) to Chicago (ORD).Boston (BOS)Chicago (ORD)American Airlines, nonstop.Departing on Sat, Oct 24 at 1:33pm from Boston, arriving at 3:37pm in Chicago.Sat, Oct 24Returning on Tue, Oct 27 at 3:15pm from Chicago, arriving at 6:35pm in Boston.Tue, Oct 27
American Airlines•NonstopAmerican AirlinesSelect American Airlines flight departing on Sat, Oct 24 at 1:33pm from Boston, returning on Tue, Oct 27 at 3:15pm from Chicago priced at $2583-day tripfound 18 hours ago30% less than typical$258$258 - Boston (BOS) to Chicago (ORD).Boston (BOS)Chicago (ORD)Delta, nonstop.Departing on Tue, Nov 3 at 1:35pm from Boston, arriving at 3:27pm in Chicago.Tue, Nov 3Returning on Sun, Nov 15 at 7:05am from Chicago, arriving at 10:32am in Boston.Sun, Nov 15
Delta•NonstopDeltaSelect Delta flight departing on Tue, Nov 3 at 1:35pm from Boston, returning on Sun, Nov 15 at 7:05am from Chicago priced at $25811-day tripfound 6 hours ago20% less than typical$258$258 - Boston (BOS) to Chicago (ORD).Boston (BOS)Chicago (ORD)JetBlue Airways, nonstop.Departing on Fri, Oct 23 at 6:55am from Boston, arriving at 8:47am in Chicago.Fri, Oct 23Returning on Mon, Oct 26 at 7:10pm from Chicago, arriving at 10:53pm in Boston.Mon, Oct 26JetBlue Airways•NonstopJetBlue AirwaysSelect JetBlue Airways flight departing on Fri, Oct 23 at 6:55am from Boston, returning on Mon, Oct 26 at 7:10pm from Chicago priced at $2583-day tripfound 4 hours ago30% less than typical$258$258
Cheap Flights from Boston to Chicago (BOS-CHI)
Prices were available within the past 7 days and start at $91 for one-way flights and $192 for roundtrip, for the period specified. Prices and availability are subject to change.
Sat, Oct 24 - Tue, Oct 27
BOS
Boston
ORD
Chicago
$192
Roundtrip
Just found
Wed, Oct 21 - Mon, Oct 26
BOS
Boston
ORD
Chicago
$193
Roundtrip
Just found
Tue, Oct 27 - Sat, Oct 31
BOS
Boston
MDW
Chicago
$201
Roundtrip
Found 2 hours ago
Thu, Nov 5 - Sat, Nov 7
BOS
Boston
ORD
Chicago
$201
Roundtrip
Just found
Thu, Nov 5 - Sat, Nov 7
BOS
Boston
ORD
Chicago
$201
Roundtrip
Just found
Mon, Oct 26 - Wed, Oct 28
BOS
Boston
ORD
Chicago
$201
Roundtrip
Just found
Mon, Oct 26 - Wed, Oct 28
BOS
Boston
ORD
Chicago
$211
Roundtrip
Just found
Thu, Dec 10 - Wed, Dec 16
BOS
Boston
ORD
Chicago
$222
Roundtrip
Just found
Thu, Dec 17 - Fri, Dec 25
BOS
Boston
ORD
Chicago
$426
Roundtrip
Found 20 hours ago
Tue, Nov 3 - Sat, Nov 7
BOS
Boston
ORD
Chicago
$499
Roundtrip
Just found
Alternative airports near Chicago
Prices were available within the past 7 days. Prices and availability are subject to change.
Find the cheapest month to fly from Boston (BOS) to Chicago (CHI)
November is typically the cheapest month to flyNovember is typically the cheapest month to fly
From $179 - $348 per traveler.
Travel information
Origin airport | Logan International Airport |
|---|---|
Destination airport | Chicago O'Hare Intl. Airport |
Distance | 863 miles away |
Airlines serving | JetBlue Airways, American Airlines, Delta, United, Alaska Airlines, Frontier Airlines, Sun Country Airlines |
Popular airline | JetBlue Airways |
Roundtrip price | $192 |
Average flight time | 3 hours 19 mins |
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