Cheap Airfare from Boston, MA (BOS) to Chicago, IL (MDW)

All flights from Boston, MA (BOS) to Chicago, IL (MDW)

We found 67 matches for direct flights, non-stop flights, and last-minute flights between BOSand MDW. Use the table below to sort by number of connections or the time of day to find flights that leave BOS for MDW in the morning, afternoon, or evening.

Be sure to check our list of deals to see which airlines are offering special prices on airfare to Chicago, IL (MDW) or airfare from Boston, MA (BOS).

Airline	Flt.	Departs	Time	Arrives	Time	Via	Compare prices
Southwest Airlines	1024	BOS	6:00am	MDW	7:40am	nonstop
Southwest Airlines	974	BOS	8:10am	MDW	9:45am	nonstop
Southwest Airlines	482	BOS	11:50am	MDW	1:25pm	nonstop
Southwest Airlines	1050	BOS	3:25pm	MDW	5:05pm	nonstop
Southwest Airlines	3399	BOS	6:30pm	MDW	8:20pm	nonstop
Southwest Airlines	1013	BOS	6:30am	MDW	11:20am	Baltimore (BWI)
Southwest Airlines	3221	BOS	10:00am	MDW	3:00pm	Baltimore (BWI)
Southwest Airlines	806	BOS	1:05pm	MDW	4:35pm	Baltimore (BWI)
Southwest Airlines	3656	BOS	4:10pm	MDW	8:15pm	Baltimore (BWI)
Delta Air Lines	3776	BOS	6:00am	MDW	9:30am	Detroit (DTW)	Search prices
Northwest Airlines	371	BOS	6:00am	MDW	9:30am	Detroit (DTW)	Search prices
Delta Air Lines	3254	BOS	9:00am	MDW	12:09pm	Detroit (DTW)	Search prices
Northwest Airlines	375	BOS	9:00am	MDW	12:09pm	Detroit (DTW)	Search prices
Northwest Airlines	385	BOS	12:00pm	MDW	3:32pm	Detroit (DTW)	Search prices
Delta Air Lines	3782	BOS	12:00pm	MDW	3:32pm	Detroit (DTW)	Search prices
Delta Air Lines	2592	BOS	2:10pm	MDW	5:29pm	Detroit (DTW)	Search prices
Delta Air Lines	2592	BOS	2:10pm	MDW	7:13pm	Detroit (DTW)	Search prices
Northwest Airlines	377	BOS	2:10pm	MDW	7:13pm	Detroit (DTW)	Search prices
Northwest Airlines	377	BOS	2:10pm	MDW	5:29pm	Detroit (DTW)	Search prices
Northwest Airlines	651	BOS	4:15pm	MDW	7:13pm	Detroit (DTW)	Search prices
Delta Air Lines	2717	BOS	4:15pm	MDW	7:13pm	Detroit (DTW)	Search prices
Delta Air Lines	5931	BOS	6:00am	MDW	9:25am	New York (LGA)	Search prices
Delta Air Lines	5931	BOS	6:00am	MDW	10:25am	New York (LGA)	Search prices
Delta Air Lines	1373	BOS	6:30am	MDW	10:25am	New York (LGA)	Search prices
Delta Air Lines	1375	BOS	7:30am	MDW	12:25pm	New York (LGA)	Search prices
Delta Air Lines	1377	BOS	8:30am	MDW	12:25pm	New York (LGA)	Search prices
Delta Air Lines	1379	BOS	9:30am	MDW	2:25pm	New York (LGA)	Search prices
Delta Air Lines	1381	BOS	10:30am	MDW	2:25pm	New York (LGA)	Search prices
Delta Air Lines	1383	BOS	11:30am	MDW	4:25pm	New York (LGA)	Search prices
Delta Air Lines	1385	BOS	12:30pm	MDW	4:25pm	New York (LGA)	Search prices
Delta Air Lines	1387	BOS	1:30pm	MDW	6:25pm	New York (LGA)	Search prices
Delta Air Lines	1389	BOS	2:30pm	MDW	7:25pm	New York (LGA)	Search prices
Delta Air Lines	1389	BOS	2:30pm	MDW	6:25pm	New York (LGA)	Search prices
Delta Air Lines	1391	BOS	3:30pm	MDW	7:25pm	New York (LGA)	Search prices
Delta Air Lines	1391	BOS	3:30pm	MDW	7:25pm	New York (LGA)	Search prices
Delta Air Lines	1393	BOS	4:30pm	MDW	9:25pm	New York (LGA)	Search prices
Delta Air Lines	1395	BOS	5:30pm	MDW	9:25pm	New York (LGA)	Search prices
Northwest Airlines	1401	BOS	6:05am	MDW	12:43pm	Minneapolis (MSP)	Search prices
Delta Air Lines	3788	BOS	6:05am	MDW	10:33am	Minneapolis (MSP)	Search prices
Northwest Airlines	1401	BOS	6:05am	MDW	10:33am	Minneapolis (MSP)	Search prices
Northwest Airlines	1401	BOS	6:05am	MDW	12:43pm	Minneapolis (MSP)	Search prices
Delta Air Lines	3788	BOS	6:05am	MDW	12:43pm	Minneapolis (MSP)	Search prices
Delta Air Lines	3788	BOS	6:05am	MDW	10:33am	Minneapolis (MSP)	Search prices
Delta Air Lines	3788	BOS	6:05am	MDW	12:43pm	Minneapolis (MSP)	Search prices
Northwest Airlines	1401	BOS	6:05am	MDW	10:33am	Minneapolis (MSP)	Search prices
Delta Air Lines	3792	BOS	8:10am	MDW	12:43pm	Minneapolis (MSP)	Search prices
Northwest Airlines	1405	BOS	8:10am	MDW	12:43pm	Minneapolis (MSP)	Search prices
Northwest Airlines	1405	BOS	8:10am	MDW	12:43pm	Minneapolis (MSP)	Search prices
Delta Air Lines	3792	BOS	8:10am	MDW	2:51pm	Minneapolis (MSP)	Search prices
Delta Air Lines	3792	BOS	8:10am	MDW	2:51pm	Minneapolis (MSP)	Search prices
Northwest Airlines	1405	BOS	8:10am	MDW	2:51pm	Minneapolis (MSP)	Search prices
Delta Air Lines	3792	BOS	8:10am	MDW	12:43pm	Minneapolis (MSP)	Search prices
Delta Air Lines	3792	BOS	8:10am	MDW	2:03pm	Minneapolis (MSP)	Search prices
Northwest Airlines	1405	BOS	8:10am	MDW	2:51pm	Minneapolis (MSP)	Search prices
Northwest Airlines	1405	BOS	8:10am	MDW	2:03pm	Minneapolis (MSP)	Search prices
Northwest Airlines	1405	BOS	8:10am	MDW	2:03pm	Minneapolis (MSP)	Search prices
Delta Air Lines	3792	BOS	8:10am	MDW	2:03pm	Minneapolis (MSP)	Search prices
Northwest Airlines	1403	BOS	11:30am	MDW	4:29pm	Minneapolis (MSP)	Search prices
Northwest Airlines	1403	BOS	11:30am	MDW	4:29pm	Minneapolis (MSP)	Search prices
Delta Air Lines	3790	BOS	11:30am	MDW	4:29pm	Minneapolis (MSP)	Search prices
Delta Air Lines	3790	BOS	11:30am	MDW	4:29pm	Minneapolis (MSP)	Search prices
Northwest Airlines	1407	BOS	1:05pm	MDW	6:35pm	Minneapolis (MSP)	Search prices
Delta Air Lines	3794	BOS	1:05pm	MDW	6:35pm	Minneapolis (MSP)	Search prices
Delta Air Lines	3794	BOS	1:05pm	MDW	6:35pm	Minneapolis (MSP)	Search prices
Northwest Airlines	1407	BOS	1:05pm	MDW	6:35pm	Minneapolis (MSP)	Search prices
Porter Airlines	940	BOS	9:05am	MDW	12:25pm	Toronto (YTZ)	Search prices
Porter Airlines	940	BOS	9:05am	MDW	12:25pm	Toronto (YTZ)	Search prices

BOS: Logan International Airport
BWI: Balt./Wash. International Airport
DTW: Wayne County Airport
LGA: La Guardia Airport
MDW: Midway Airport
MSP: St Paul International Airport
YTZ: Toronto Island Airport

Note: Southwest Airlines tickets can be purchsed at Southwest.com.

Delta Air Lines
Phone #: 800-221-1212
URL: http://www.delta.com
Northwest Airlines
Phone #: 800-225-2525
URL: http://www.nwa.com
Porter Airlines
Phone #:
URL: http://www.flyporter.com
Southwest Airlines
Phone #: 800-435-9792
URL: http://www.iflyswa.com

For more options, try adding these alternate airports :

Or check your return flight :

Disclaimer

Smarter Travel Media LLC and Innovata, LLC have used their best efforts to collect and prepare material for inclusion in this travel directory, and cannot warrant that the information is totally complete or accurate.

Data shown in this directory are for information only. Neither Innovata nor Smarter Travel Media LLC will be responsible for the failure of flights to operate at the times listed in this publication, nor for errors herein, nor for failure to make connections with planes, nor for any omissions of data.

Schedules are subject to change without notice. Schedules shown are based on expected flight times as presented to Smarter Travel Media LLC. Weather and other factors may affect operating conditions, and departures and arrivals cannot be guaranteed. The mileage shown is approximate, based on industry standards, and will vary from actual airline mileage received for each flight segment.

Smarter Travel Media LLC and Innovata disclaim any liability to any person for loss or damage caused by errors or omissions in the data contained on this page, whether such errors or omissions result from negligence, accident or other cause.

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Other Flights From BOS

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Cheap airfare from BOS to MLM (4 flights)

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Greensboro combines a small-town feel with big-city attractions.

Hotels

Crowne Plaza Campbell House
1375 South Broadway
Lexington, KY
5 traveler comments
Number of Rooms: 290
Holiday Inn Indianapolis East
6990 E. 21st Street
I70 & Shadeland Avenue
Indianapolis, IN
5 traveler comments
Number of Rooms: 184
Number of Floors: 6
Red Roof Inn Columbus Ohio State University
441 Ackerman Road
Columbus, OH
5 traveler comments
Number of Rooms: 115
Doubletree Hotel Chattanooga
407 Chestnut Street
Chattanooga, TN
5 traveler comments
Number of Rooms: 186
Number of Floors: 12
Country Inn & Suites University Place
131 E McCullough Dr
Charlotte, NC
5 traveler comments
Number of Rooms: 100
Number of Floors: 3
Charlotte Marriott City Center
100 West Trade St
Charlotte, NC
5 traveler comments
Number of Rooms: 438
Number of Floors: 19
Doubletree Hotel Charlotte - Gateway Village
895 W Trade St
Charlotte, NC
5 traveler comments
Number of Rooms: 187
Hampton Inn & Suites Boston Crosstown Center
811 Massachusetts Avenue
Boston, MA
5 traveler comments
Number of Rooms: 175
Renaissance Waverly Hotel
2450 Galleria Pkwy
Atlanta, GA
5 traveler comments
Number of Rooms: 521
Number of Floors: 14
Crowne Plaza Atlanta Airport
1325 Virginia Avenue
Atlanta, GA
5 traveler comments

From:		Month:
To:		Day:

Current departures: Boston (BOS) Manchester (MHT) [45 miles from BOS] Provincetown (PVC) [45 miles from BOS] Worcester (ORH) [45 miles from BOS] New Bedford (EWB) [48 miles from BOS] Providence (PVD) [49 miles from BOS]	Current arrivals: Chicago (MDW) Chicago (CGX) [9 miles from MDW] Chicago (ORD) [16 miles from MDW]