Cheap flights from TPA to MDW (Tampa Intl. to Midway Intl.)

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Cheap Flights from TPA to MDW starting at $74 One Way, $163 Round Trip

Prices starting at $163 for return flights and $74 for one-way flights to Midway Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, May 1 - Wed, May 6
TPA
Tampa
MDW
Chicago
$163 Roundtrip, found 2 hours ago
$163
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Fri, May 1 from Tampa to Chicago, returning Wed, May 6, priced at $163 found 2 hours ago
Sat, May 9 - Mon, May 11
TPA
Tampa
MDW
Chicago
$176 Roundtrip, found 5 hours ago
$176
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, May 9 from Tampa to Chicago, returning Mon, May 11, priced at $176 found 5 hours ago
Sat, May 2 - Wed, May 6
TPA
Tampa
MDW
Chicago
$182 Roundtrip, found 1 day ago
$182
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 2 from Tampa to Chicago, returning Wed, May 6, priced at $182 found 1 day ago
Wed, May 6 - Sun, May 10
TPA
Tampa
MDW
Chicago
$201 Roundtrip, found 3 days ago
$201
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, May 6 from Tampa to Chicago, returning Sun, May 10, priced at $201 found 3 days ago
Thu, May 28 - Mon, Jun 1
TPA
Tampa
MDW
Chicago
$203 Roundtrip, found 5 hours ago
$203
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Thu, May 28 from Tampa to Chicago, returning Mon, Jun 1, priced at $203 found 5 hours ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$103 nightly
The price is $121 total per night from Apr 1 to Apr 2
$121 total
Apr 1 - Apr 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (9,973 reviews)
Clean room

Reviewed on Mar 20, 2026

Congress Plaza Hotel
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
$116 nightly
The price is $136 total per night from Mar 22 to Mar 23
$136 total
Mar 22 - Mar 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,002 reviews)
Nice location for bus travelers and connection by metro

Reviewed on Mar 18, 2026

Holiday Inn & Suites Chicago - Downtown by IHG
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
$125 nightly
The price is $147 total per night from Mar 29 to Mar 30
$147 total
Mar 29 - Mar 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
9/10 Wonderful! (2,017 reviews)
Everything was good, except on the 2nd day, the drains to the shower and sink were very clogged. Took some minutes before the water went down all the way.

Reviewed on Mar 20, 2026

Crowne Plaza Chicago West Loop by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$103 nightly
The price is $121 total per night from Apr 1 to Apr 2
$121 total
Apr 1 - Apr 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (9,973 reviews)
Clean room

Reviewed on Mar 20, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$156 nightly
The price is $183 total per night from Apr 6 to Apr 7
$183 total
Apr 6 - Apr 7
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (3,574 reviews)
The breakfast was incredibly delicious. The hotel in general is a 10 out of 10.

Reviewed on Mar 20, 2026

Hotel Riu Plaza Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
$130 nightly
The price is $153 total per night from Mar 29 to Mar 30
$153 total
Mar 29 - Mar 30
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,752 reviews)
The breakfast was delicious with made to order omelettes and fountain soda! Lots of great open common space and very spacious rooms. Attention to detail with cleaning of the rooms could be better.

Reviewed on Mar 20, 2026

Embassy Suites by Hilton Chicago Downtown River North
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chicago Hotels With Airport Transportation

Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave Elk Grove Village IL
$55 nightly
The price is $62 total per night from Mar 25 to Mar 26
$62 total
Mar 25 - Mar 26
Total with taxes and fees
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,877 reviews)
Staff can Sametimes be very rude. I stayed at Motel 6 in Bridgeview IL and got to stay 3 months now you can only stay 14 days before having to leave and wait 72 hours before you can come back. It's really different now especially when you are homeless.

Reviewed on Mar 19, 2026

Motel 6 Elk Grove Village, IL - O'Hare
Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
777 E Grand Avenue Bensenville IL
$96 nightly
The price is $107 total per night from Apr 5 to Apr 6
$107 total
Apr 5 - Apr 6
Total with taxes and fees
Book a stay at this golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.4/10 Good! (1,309 reviews)
Wery nice place to stay

Reviewed on Mar 20, 2026

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
O'Hare Inn & Suites

O'Hare Inn & Suites

2 out of 5
4101 Mannheim Rd Schiller Park IL
$64 nightly
The price is $72 total per night from Mar 23 to Mar 24
$72 total
Mar 23 - Mar 24
Total with taxes and fees
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Allstate Arena and Fashion ...
5.8/10 (1,000 reviews)
Literally the worst place! We showed up at 11PM and they had cancelled our room without telling us. Manager did not want to help and we were stuck without a hotel room for the night. STAY AWAY!

Reviewed on Mar 19, 2026

O'Hare Inn & Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Chicago Hotels

Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
The price is $94 total per night from Mar 24 to Mar 25
$94 total
per night
Mar 24 - Mar 25
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (2,812 reviews)
Great experience

Reviewed on Mar 19, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
The price is $121 total per night from Mar 29 to Mar 30
$121 total
per night
Mar 29 - Mar 30
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
7.4/10 Good! (2,525 reviews)
It’s was good for a last minute stay. Nothing special, nothing bad.

Reviewed on Mar 17, 2026

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave Elk Grove Village IL
The price is $62 total per night from Mar 25 to Mar 26
$62 total
per night
Mar 25 - Mar 26
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,877 reviews)
Staff can Sametimes be very rude. I stayed at Motel 6 in Bridgeview IL and got to stay 3 months now you can only stay 14 days before having to leave and wait 72 hours before you can come back. It's really different now especially when you are homeless.

Reviewed on Mar 19, 2026

Motel 6 Elk Grove Village, IL - O'Hare
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4 out of 5
511 North Columbus Drive Chicago IL
$144 nightly
The price is $169 total per night from Apr 6 to Apr 7
$169 total
Apr 6 - Apr 7
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (2,795 reviews)
Two of four elevators were out so made going up and down a lengthy process.. we had 2/6 days where we didn’t get a towel refresh as the housekeeper said she didn’t have any to offer. (Full house). Breakfast is the reason you stay here- it was excellent, didn’t run out and the made to order was fantastic! ...

Reviewed on Mar 20, 2026

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
$159 nightly
The price is $183 total per night from Apr 5 to Apr 6
$183 total
Apr 5 - Apr 6
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,326 reviews)
Beautiful property, great resturant on site, an the pool and spa was amazing.

Reviewed on Mar 18, 2026

Palmer House a Hilton Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
$130 nightly
The price is $153 total per night from Mar 29 to Mar 30
$153 total
Mar 29 - Mar 30
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,752 reviews)
The breakfast was delicious with made to order omelettes and fountain soda! Lots of great open common space and very spacious rooms. Attention to detail with cleaning of the rooms could be better.

Reviewed on Mar 20, 2026

Embassy Suites by Hilton Chicago Downtown River North
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

TPA to MDW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
TPA Address & GPS
Address:
5507 West Spruce Street
Tampa FL, 33607
United States
IATA Code:
TPA
Longitude:
-82.535415
Latitude:
27.979869
Time Zone:
America/New_York
MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago

Frequently asked questions

Are there non-stop flights from Tampa Airport to Midway Airport?
If you're not a huge fan of layovers, we've got very good news for you. There are multiple air carriers that offer direct flights from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW), including Southwest Airlines and Frontier Airlines.
What is the shortest flight from Tampa Intl. Airport (TPA) to Chicago Airport?
It can take as little as 2 hours and 45 minutes to fly from Tampa Airport to Midway Intl. Airport (MDW). Take a seat and enjoy those window views, because you'll be landing before long.
How many hours flight from Tampa Airport to Midway Intl. Airport (MDW)?
There's no reason not to book a Chicago escape when the flight time from TPA to MDW is just 2 hours and 47 minutes on average. Go ahead and grab a ticket — it's about time you finally took a break.
What airlines have the most flights from Tampa Airport to Chicago Airport?
While there are several airlines that have flights from Tampa Airport to Midway Intl. Airport (MDW), there are a couple that stand out in the popularity stakes. Frontier Airlines (F9) is one of the favorites and has 23 flights every month. Southwest Airlines (WN) also flies from Tampa to Chicago. It's another popular choice and has 123 flights each month.

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

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