Skip navigation

Cheap Airfare, Vacation Deals, Car Rental, and Discount Travel - SmarterTravel.com
User's Avatar
My SmarterTravel

Cheap Airfare from Tampa, FL (TPA) to Chicago, IL (MDW)

All flights from Tampa, FL (TPA) to Chicago, IL (MDW)

We found 109 matches for direct flights, non-stop flights, and last-minute flights between TPAand MDW. Use the table below to sort by number of connections or the time of day to find flights that leave TPA 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 Tampa, FL (TPA).

Airline Flt. Departs Time Arrives Time sort Via Compare prices
Southwest Airlines 2470 TPA 8:20am MDW 10:00am nonstop
Southwest Airlines 1801 TPA 8:30am MDW 11:05am direct
Southwest Airlines 1027 TPA 9:25am MDW 12:05pm direct
Southwest Airlines 112 TPA 9:50am MDW 11:30am nonstop
Southwest Airlines 232 TPA 12:15pm MDW 1:55pm nonstop
Southwest Airlines 1377 TPA 12:35pm MDW 2:15pm nonstop
Southwest Airlines 1824 TPA 1:55pm MDW 4:30pm direct
Southwest Airlines 3714 TPA 2:50pm MDW 4:30pm nonstop
Southwest Airlines 352 TPA 3:05pm MDW 6:50pm direct
Southwest Airlines 721 TPA 4:50pm MDW 6:30pm nonstop
Southwest Airlines 208 TPA 6:00pm MDW 7:40pm nonstop
AirTran 132 TPA 6:00am MDW 9:06am Atlanta (ATL) Search prices
AirTran 132 TPA 6:00am MDW 10:16am Atlanta (ATL) Search prices
Delta Air Lines 2056 TPA 6:30am MDW 11:50am Atlanta (ATL) Search prices
AirTran 120 TPA 7:15am MDW 12:01pm Atlanta (ATL) Search prices
AirTran 120 TPA 7:15am MDW 10:16am Atlanta (ATL) Search prices
Delta Air Lines 2058 TPA 7:30am MDW 11:50am Atlanta (ATL) Search prices
AirTran 122 TPA 8:28am MDW 12:01pm Atlanta (ATL) Search prices
Delta Air Lines 2060 TPA 8:30am MDW 11:50am Atlanta (ATL) Search prices
Delta Air Lines 2060 TPA 8:30am MDW 1:14pm Atlanta (ATL) Search prices
Delta Air Lines 2062 TPA 9:55am MDW 1:14pm Atlanta (ATL) Search prices
Delta Air Lines 2062 TPA 9:55am MDW 2:30pm Atlanta (ATL) Search prices
Delta Air Lines 2064 TPA 11:01am MDW 2:30pm Atlanta (ATL) Search prices
Delta Air Lines 2064 TPA 11:01am MDW 3:34pm Atlanta (ATL) Search prices
AirTran 118 TPA 11:37am MDW 4:40pm Atlanta (ATL) Search prices
Delta Air Lines 2066 TPA 1:00pm MDW 5:00pm Atlanta (ATL) Search prices
Delta Air Lines 2066 TPA 1:00pm MDW 6:25pm Atlanta (ATL) Search prices
Delta Air Lines 2068 TPA 1:20pm MDW 5:00pm Atlanta (ATL) Search prices
Delta Air Lines 2068 TPA 1:20pm MDW 6:25pm Atlanta (ATL) Search prices
AirTran 118 TPA 1:35pm MDW 5:54pm Atlanta (ATL) Search prices
AirTran 118 TPA 1:35pm MDW 4:40pm Atlanta (ATL) Search prices
AirTran 121 TPA 2:42pm MDW 5:54pm Atlanta (ATL) Search prices
AirTran 121 TPA 2:42pm MDW 8:04pm Atlanta (ATL) Search prices
Delta Air Lines 2070 TPA 4:00pm MDW 7:40pm Atlanta (ATL) Search prices
AirTran 159 TPA 4:12pm MDW 8:04pm Atlanta (ATL) Search prices
Delta Air Lines 22 TPA 5:10pm MDW 10:19pm Atlanta (ATL) Search prices
Delta Air Lines 2074 TPA 6:20pm MDW 10:19pm Atlanta (ATL) Search prices
AirTran 129 TPA 6:40pm MDW 11:05pm Atlanta (ATL) Search prices
AirTran 129 TPA 6:40pm MDW 9:50pm Atlanta (ATL) Search prices
Delta Air Lines 2074 TPA 6:50pm MDW 10:19pm Atlanta (ATL) Search prices
AirTran 128 TPA 7:47pm MDW 11:05pm Atlanta (ATL) Search prices
Southwest Airlines 560 TPA 10:10am MDW 12:55pm Nashville (BNA)
Southwest Airlines 1896 TPA 4:50pm MDW 7:40pm Nashville (BNA)
Southwest Airlines 244 TPA 5:15pm MDW 9:30pm Nashville (BNA)
Southwest Airlines 168 TPA 6:45pm MDW 9:30pm Nashville (BNA)
Southwest Airlines 468 TPA 10:00am MDW 1:35pm Buffalo (BUF)
Southwest Airlines 3948 TPA 7:00am MDW 11:20am Baltimore (BWI)
Southwest Airlines 1717 TPA 8:05am MDW 1:00pm Baltimore (BWI)
Southwest Airlines 1395 TPA 10:15am MDW 3:00pm Baltimore (BWI)
Southwest Airlines 1409 TPA 10:35am MDW 2:55pm Baltimore (BWI)
Southwest Airlines 1891 TPA 12:55pm MDW 5:25pm Baltimore (BWI)
Southwest Airlines 1151 TPA 1:05pm MDW 6:50pm Baltimore (BWI)
Southwest Airlines 352 TPA 3:05pm MDW 8:15pm Baltimore (BWI)
Southwest Airlines 1027 TPA 9:25am MDW 1:15pm Columbus (CMH)
Southwest Airlines 1028 TPA 9:40am MDW 12:45pm Columbus (CMH)
Southwest Airlines 1096 TPA 1:20pm MDW 4:15pm Columbus (CMH)
Southwest Airlines 2260 TPA 2:25pm MDW 5:45pm Columbus (CMH)
Delta Air Lines 3081 TPA 6:45am MDW 12:09pm Detroit (DTW) Search prices
Northwest Airlines 491 TPA 6:45am MDW 12:09pm Detroit (DTW) Search prices
Delta Air Lines 2645 TPA 11:55am MDW 5:29pm Detroit (DTW) Search prices
Northwest Airlines 493 TPA 11:55am MDW 3:32pm Detroit (DTW) Search prices
Delta Air Lines 2645 TPA 11:55am MDW 5:46pm Detroit (DTW) Search prices
Northwest Airlines 493 TPA 11:55am MDW 5:46pm Detroit (DTW) Search prices
Delta Air Lines 2645 TPA 11:55am MDW 3:32pm Detroit (DTW) Search prices
Northwest Airlines 493 TPA 11:55am MDW 5:29pm Detroit (DTW) Search prices
Northwest Airlines 485 TPA 3:30pm MDW 7:13pm Detroit (DTW) Search prices
Delta Air Lines 3076 TPA 3:30pm MDW 7:13pm Detroit (DTW) Search prices
Southwest Airlines 995 TPA 7:55am MDW 11:55am Fort Lauderdale (FLL)
Southwest Airlines 566 TPA 10:35am MDW 2:55pm Fort Lauderdale (FLL)
Southwest Airlines 3111 TPA 10:35am MDW 3:25pm Fort Lauderdale (FLL)
Southwest Airlines 2876 TPA 3:15pm MDW 7:10pm Fort Lauderdale (FLL)
Southwest Airlines 1635 TPA 3:35pm MDW 7:15pm Fort Lauderdale (FLL)
Southwest Airlines 10 TPA 6:55am MDW 11:15am Houston (HOU)
Southwest Airlines 3605 TPA 9:10am MDW 2:30pm Houston (HOU)
Southwest Airlines 3605 TPA 9:10am MDW 4:00pm Houston (HOU)
Southwest Airlines 750 TPA 11:40am MDW 5:40pm Houston (HOU)
Southwest Airlines 1783 TPA 4:05pm MDW 10:50pm Houston (HOU)
Southwest Airlines 1783 TPA 4:05pm MDW 8:45pm Houston (HOU)
Southwest Airlines 2628 TPA 10:55am MDW 3:05pm Washington (IAD)
Southwest Airlines 627 TPA 12:55pm MDW 5:40pm Washington (IAD)
Southwest Airlines 627 TPA 12:55pm MDW 6:50pm Washington (IAD)
Southwest Airlines 3040 TPA 1:10pm MDW 4:45pm Indianapolis (IND)
Southwest Airlines 3885 TPA 2:05pm MDW 6:30pm Indianapolis (IND)
Southwest Airlines 181 TPA 10:05am MDW 3:45pm Kansas City (MCI)
Southwest Airlines 181 TPA 10:05am MDW 3:00pm Kansas City (MCI)
Southwest Airlines 1441 TPA 11:25am MDW 5:15pm Kansas City (MCI)
Southwest Airlines 1441 TPA 11:25am MDW 2:55pm Kansas City (MCI)
Southwest Airlines 1109 TPA 4:05pm MDW 7:30pm Kansas City (MCI)
Southwest Airlines 1109 TPA 4:05pm MDW 8:40pm Kansas City (MCI)
Northwest Airlines 435 TPA 1:50pm MDW 6:35pm Minneapolis (MSP) Search prices
Northwest Airlines 435 TPA 1:50pm MDW 6:35pm Minneapolis (MSP) Search prices
Northwest Airlines 435 TPA 1:50pm MDW 8:12pm Minneapolis (MSP) Search prices
Northwest Airlines 435 TPA 1:50pm MDW 8:12pm Minneapolis (MSP) Search prices
Delta Air Lines 3055 TPA 1:50pm MDW 8:12pm Minneapolis (MSP) Search prices
Delta Air Lines 3055 TPA 1:50pm MDW 8:12pm Minneapolis (MSP) Search prices
Delta Air Lines 3055 TPA 1:50pm MDW 6:35pm Minneapolis (MSP) Search prices
Delta Air Lines 3055 TPA 1:50pm MDW 6:35pm Minneapolis (MSP) Search prices
Southwest Airlines 766 TPA 8:40am MDW 2:55pm Philadelphia (PHL)
Southwest Airlines 3416 TPA 10:05am MDW 4:35pm Philadelphia (PHL)
Southwest Airlines 248 TPA 1:35pm MDW 7:45pm Philadelphia (PHL)
Southwest Airlines 248 TPA 1:35pm MDW 6:35pm Philadelphia (PHL)
Southwest Airlines 422 TPA 12:05pm MDW 5:25pm Pittsburgh (PIT)
Southwest Airlines 1143 TPA 2:30pm MDW 6:35pm Raleigh/Durham (RDU)
Southwest Airlines 2267 TPA 11:15am MDW 3:15pm Louisville (SDF)
Southwest Airlines 3914 TPA 11:25am MDW 3:10pm Saint Louis (STL)
Southwest Airlines 3914 TPA 11:25am MDW 4:10pm Saint Louis (STL)
Southwest Airlines 3914 TPA 11:25am MDW 3:35pm Saint Louis (STL)
Southwest Airlines 494 TPA 4:30pm MDW 8:20pm Saint Louis (STL)
Southwest Airlines 494 TPA 4:30pm MDW 8:20pm Saint Louis (STL)

ATL: Hartsfield-Jackson Atlanta International Airport
BNA: Nashville Metropolitan Airport
BUF: Buffalo Niagara International Airport
BWI: Balt./Wash. International Airport
CMH: Port Columbus International Airport
DTW: Wayne County Airport
FLL: Ft. Lauderdale International Airport
HOU: Hobby Airport
IAD: Dulles International Airport
IND: Indianapolis International Airport
MCI: Kansas City International Airport
MDW: Midway Airport
MSP: St Paul International Airport
PHL: Philadelphia International Airport
PIT: Pittsburgh International Airport
RDU: Raleigh/Durham Airport
SDF: Standiford Field
STL: Lambert-St. Louis International Airport
TPA: Tampa International Airport

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

AirTran
Phone #: 800-247-8726
URL: http://www.airtran.com
Delta Air Lines
Phone #: 800-221-1212
URL: http://www.delta.com
Northwest Airlines
Phone #: 800-225-2525
URL: http://www.nwa.com
Southwest Airlines
Phone #: 800-435-9792
URL: http://www.iflyswa.com

For more options, try adding these alternate airports :

Current departures:
Tampa (TPA)
Tampa (PIE) [10 miles from TPA]
Sarasota (SRQ) [40 miles from TPA]
Current arrivals:
Chicago (MDW)
Chicago (CGX) [9 miles from MDW]
Chicago (ORD) [16 miles from MDW]

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.

ALERT!
Your pop-up blocker security
setting is too high.



To view this page and still use your pop-up blocker, please make the following adjustment to Internet Explorer.

- Click on "Tools"
- Click on "Pop-up Blocker"
- Click on "Always Allow Pop-ups from This Site..."
- Try the link again

If you are not using Internet Explorer or are still having issues, please email feedback@smartertravel.com with details

Other Flights From TPA

FREE SMARTERTRAVEL NEWSLETTER!
Get the early word on the latest travel deals of the day picked by our editors. Sign up for our free Deal Alert newsletter.
Advertisement

Destinations

Hotels