$118 Cheap Flights from Boston (BOS) to Chicago (CHI)
Popular airlines from Logan International Airport (BOS) to Chicago
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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 10:05pm from Chicago, arriving on Tue, Oct 13 at 10:15am 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 10:05pm from Chicago priced at $5063-day tripfound 14 hours ago60% less than typical$506$506 - Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Wed, Oct 7 at 4:20pm from Boston, arriving at 5:55pm in Chicago.Wed, Oct 7Returning on Sun, Oct 11 at 5:00am from Chicago, arriving at 8:25am in Boston.Sun, Oct 11Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Wed, Oct 7 at 4:20pm from Boston, returning on Sun, Oct 11 at 5:00am from Chicago priced at $3973-day tripfound 12 hours ago55% less than typical$397$397
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Mon, Oct 12 at 5:50am from Boston, arriving at 7:25am in Chicago.Mon, Oct 12Returning on Fri, Oct 16 at 6:45pm from Chicago, arriving at 10:05pm in Boston.Fri, Oct 16Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Mon, Oct 12 at 5:50am from Boston, returning on Fri, Oct 16 at 6:45pm from Chicago priced at $3564-day tripfound 12 hours ago55% less than typical$356$356
- 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 1:15pm from Chicago, arriving at 4:20pm 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 1:15pm from Chicago priced at $2955-day tripfound 21 hours ago55% less than typical$295$295
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Thu, Nov 5 at 12:45pm from Boston, arriving at 2:30pm in Chicago.Thu, Nov 5Returning on Wed, Nov 11 at 1:15pm from Chicago, arriving at 4:20pm in Boston.Wed, Nov 11Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Thu, Nov 5 at 12:45pm from Boston, returning on Wed, Nov 11 at 1:15pm from Chicago priced at $3156-day tripfound 3 hours ago55% less than typical$315$315
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Mon, Nov 9 at 12:45pm from Boston, arriving at 2:30pm in Chicago.Mon, Nov 9Returning on Thu, Nov 12 at 6:45pm from Chicago, arriving at 10:05pm in Boston.Thu, Nov 12Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Mon, Nov 9 at 12:45pm from Boston, returning on Thu, Nov 12 at 6:45pm from Chicago priced at $3153-day tripfound 2 hours ago50% less than typical$315$315
- Boston (BOS) to Chicago (ORD).Boston (BOS)Chicago (ORD)American Airlines, nonstop.Departing on Sun, Oct 11 at 5:54am from Boston, arriving at 8:00am in Chicago.Sun, Oct 11Returning on Sun, Oct 18 at 6:00am from Chicago, arriving at 9:37am in Boston.Sun, Oct 18
American Airlines•NonstopAmerican AirlinesSelect American Airlines flight departing on Sun, Oct 11 at 5:54am from Boston, returning on Sun, Oct 18 at 6:00am from Chicago priced at $3567-day tripfound 19 hours ago25% less than typical$356$356 - Boston (BOS) to Chicago (ORD).Boston (BOS)Chicago (ORD)American Airlines, nonstop.Departing on Thu, Oct 22 at 7:00am from Boston, arriving at 9:05am in Chicago.Thu, Oct 22Returning on Sun, Oct 25 at 6:29am from Chicago, arriving at 12:18pm in Boston.Sun, Oct 25American Airlines•NonstopAmerican AirlinesSelect American Airlines flight departing on Thu, Oct 22 at 7:00am from Boston, returning on Sun, Oct 25 at 6:29am from Chicago priced at $3253-day tripfound 11 hours ago25% less than typical$325$325
- Boston (BOS) to Chicago (ORD).Boston (BOS)Chicago (ORD)American Airlines, nonstop.Departing on Fri, Oct 16 at 5:54am from Boston, arriving at 8:00am in Chicago.Fri, Oct 16Returning on Fri, Oct 23 at 7:03pm from Chicago, arriving at 10:37pm in Boston.Fri, Oct 23American Airlines•NonstopAmerican AirlinesSelect American Airlines flight departing on Fri, Oct 16 at 5:54am from Boston, returning on Fri, Oct 23 at 7:03pm from Chicago priced at $3157-day tripfound 4 hours ago25% less than typical$315$315
- Boston (BOS) to Chicago (ORD).Boston (BOS)Chicago (ORD)American Airlines, nonstop.Departing on Thu, Oct 29 at 8:23am from Boston, arriving at 10:30am in Chicago.Thu, Oct 29Returning on Sun, Nov 1 at 5:52pm from Chicago, arriving at 9:26pm in Boston.Sun, Nov 1American Airlines•NonstopAmerican AirlinesSelect American Airlines flight departing on Thu, Oct 29 at 8:23am from Boston, returning on Sun, Nov 1 at 5:52pm from Chicago priced at $3153-day tripfound 8 hours ago25% less than typical$315$315
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Thu, Oct 29 at 7:05am from Boston, arriving at 8:40am in Chicago.Thu, Oct 29Returning on Sun, Nov 1 at 7:50am from Chicago, arriving at 11:10am in Boston.Sun, Nov 1Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Thu, Oct 29 at 7:05am from Boston, returning on Sun, Nov 1 at 7:50am from Chicago priced at $3153-day tripfound 10 hours ago25% less than typical$315$315
- 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 Sun, Nov 1 at 7:50am from Chicago, arriving at 11:10am in Boston.Sun, Nov 1Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Thu, Oct 29 at 5:50am from Boston, returning on Sun, Nov 1 at 7:50am from Chicago priced at $3153-day tripfound 10 hours ago25% less than typical$315$315
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Thu, Nov 5 at 6:30pm from Boston, arriving at 8:15pm 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 6:30pm from Boston, returning on Wed, Nov 11 at 8:30am from Chicago priced at $2955-day tripfound 20 hours ago25% less than typical$295$295
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Thu, Oct 15 at 7:05am from Boston, arriving at 8:40am in Chicago.Thu, Oct 15Returning on Thu, Oct 22 at 5:30am from Chicago, arriving at 8:55am in Boston.Thu, Oct 22Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Thu, Oct 15 at 7:05am from Boston, returning on Thu, Oct 22 at 5:30am from Chicago priced at $3056-day tripfound 23 hours ago20% less than typical$305$305
- Boston (BOS) to Chicago (MDW).Boston (BOS)Chicago (MDW)Southwest Airlines, nonstop.Departing on Sat, Oct 24 at 9:40am from Boston, arriving at 11:15am in Chicago.Sat, Oct 24Returning on Thu, Oct 29 at 3:30pm from Chicago, arriving at 6:50pm in Boston.Thu, Oct 29Southwest Airlines•NonstopSouthwest AirlinesSelect Southwest Airlines flight departing on Sat, Oct 24 at 9:40am from Boston, returning on Thu, Oct 29 at 3:30pm from Chicago priced at $3155-day tripfound 12 hours ago20% less than typical$315$315
Cheap Flights from Boston to Chicago (BOS-CHI)
Prices were available within the past 7 days and start at $118 for one-way flights and $209 for roundtrip, for the period specified. Prices and availability are subject to change.
Wed, Nov 4 - Wed, Nov 11
BOS
Boston
MDW
Chicago
$209
Roundtrip
Found 1 day ago
Wed, Nov 4 - Wed, Nov 11
BOS
Boston
MDW
Chicago
$219
Roundtrip
Found 1 day ago
Wed, Nov 4 - Wed, Nov 11
BOS
Boston
MDW
Chicago
$224
Roundtrip
Found 1 day ago
Wed, Nov 4 - Wed, Nov 11
BOS
Boston
MDW
Chicago
$229
Roundtrip
Found 1 day ago
Tue, Oct 27 - Tue, Nov 3
BOS
Boston
MDW
Chicago
$230
Roundtrip
Found 4 days ago
Tue, Oct 27 - Tue, Nov 3
BOS
Boston
MDW
Chicago
$230
Roundtrip
Found 4 days ago
Sat, Dec 12 - Thu, Dec 17
BOS
Boston
ORD
Chicago
$236
Roundtrip
Found 1 day ago
Mon, Oct 26 - Wed, Nov 4
BOS
Boston
ORD
Chicago
$239
Roundtrip
Found 2 days ago
Sat, Nov 7 - Tue, Nov 10
BOS
Boston
MDW
Chicago
$262
Roundtrip
Found 1 day ago
Thu, Oct 29 - Sat, Nov 7
BOS
Boston
ORD
Chicago
$265
Roundtrip
Found 23 hours ago
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, IL |
Distance | 882 miles away |
Roundtrip price | $209 |
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