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

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Cheap Flights from TPA to MDW starting at $61 One Way, $93 Round Trip

Prices starting at $93 for return flights and $61 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.

Sun, Nov 16 - Mon, Nov 17
TPA
Tampa
MDW
Chicago
$93 Roundtrip, found 4 days ago
$93
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Nov 16 from Tampa to Chicago, returning Mon, Nov 17, priced at $93 found 4 days ago
Wed, Nov 12 - Mon, Nov 17
TPA
Tampa
MDW
Chicago
$97 Roundtrip, found 5 days ago
$97
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Nov 12 from Tampa to Chicago, returning Mon, Nov 17, priced at $97 found 5 days ago
Mon, Nov 10 - Mon, Nov 17
TPA
Tampa
MDW
Chicago
$100 Roundtrip, found 3 days ago
$100
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Nov 10 from Tampa to Chicago, returning Mon, Nov 17, priced at $100 found 3 days ago
Thu, Nov 13 - Mon, Nov 17
TPA
Tampa
MDW
Chicago
$104 Roundtrip, found 2 days ago
$104
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Tampa to Chicago, returning Mon, Nov 17, priced at $104 found 2 days ago
Fri, Nov 7 - Sun, Nov 16
TPA
Tampa
MDW
Chicago
$108 Roundtrip, found 3 days ago
$108
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Nov 7 from Tampa to Chicago, returning Sun, Nov 16, priced at $108 found 3 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

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
$102 nightly
The price is $120 total per night from Nov 23 to Nov 24
$120 total
Nov 23 - Nov 24
Total with taxes and fees
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,628 reviews)
Nice and well organized despite a busy marathon weekend in the city. great location!

Reviewed on Oct 27, 2025

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

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street, Chicago, IL
$128 nightly
The price is $151 total per night from Nov 23 to Nov 24
$151 total
Nov 23 - Nov 24
Total with taxes and fees
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,008 reviews)
Clean, good service, and great location.

Reviewed on Oct 24, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street, Chicago, IL
$93 nightly
The price is $109 total per night from Nov 24 to Nov 25
$109 total
Nov 24 - Nov 25
Total with taxes and fees
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,696 reviews)
Very friendly staff. Hotel was kept well. Lots of things to do in the area.

Reviewed on Oct 27, 2025

Hilton Garden Inn Chicago Downtown South Loop
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

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
$127 nightly
The price is $149 total per night from Nov 16 to Nov 17
$149 total
Nov 16 - Nov 17
Total with taxes and fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (5,175 reviews)
Breakfast was organized and clean. Room was spacious

Reviewed on Oct 31, 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
$110 nightly
The price is $129 total per night from Nov 25 to Nov 26
$129 total
Nov 25 - Nov 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (9,611 reviews)
Great

Reviewed on Oct 28, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
$84 nightly
The price is $99 total per night from Nov 17 to Nov 18
$99 total
Nov 17 - Nov 18
Total with taxes and fees
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (2,550 reviews)
Great place.

Reviewed on Oct 31, 2025

Freehand Chicago
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
$52 nightly
The price is $59 total per night from Nov 16 to Nov 17
$59 total
Nov 16 - Nov 17
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! (1,666 reviews)
Clean room and staff at front desk more courteous

Reviewed on Oct 30, 2025

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
$91 nightly
The price is $101 total per night from Nov 24 to Nov 25
$101 total
Nov 24 - Nov 25
Total with taxes and fees
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
7.2/10 Good! (1,156 reviews)
The breakfast got a little boring. There were no paintings in the hotel room. Very strange. I felt like i was in a prison. All inn all i will be back. They are very friendly, helpful and made sure the breakfast item never ran out. I'll mention it again VERY wonderful staff.

Reviewed on Oct 27, 2025

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

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road, Schiller Park, IL
$76 nightly
The price is $86 total per night from Nov 23 to Nov 24
$86 total
Nov 23 - Nov 24
Total with taxes and fees
Stay at this 3-star business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
8/10 Very Good! (2,723 reviews)
Great

Reviewed on Oct 31, 2025

Comfort Suites Chicago O'Hare Airport
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
$84 nightly
The price is $99 total per night from Nov 17 to Nov 18
$99 total
Nov 17 - Nov 18
Total with taxes and fees
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (2,550 reviews)
Great place.

Reviewed on Oct 31, 2025

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
$88 nightly
The price is $103 total per night from Nov 17 to Nov 18
$103 total
Nov 17 - Nov 18
Total with taxes and fees
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 ...
7.2/10 Good! (2,430 reviews)
Very spacious room

Reviewed on Oct 27, 2025

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
$52 nightly
The price is $59 total per night from Nov 16 to Nov 17
$59 total
Nov 16 - Nov 17
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! (1,666 reviews)
Clean room and staff at front desk more courteous

Reviewed on Oct 30, 2025

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
$147 nightly
The price is $173 total per night from Nov 24 to Nov 25
$173 total
Nov 24 - Nov 25
Total with taxes and fees
Stay at this 4-star 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! (2,753 reviews)
Location to the downtown

Reviewed on Oct 31, 2025

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
$135 nightly
The price is $154 total per night from Nov 24 to Nov 25
$154 total
Nov 24 - Nov 25
Total with taxes and fees
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.4/10 Very Good! (2,043 reviews)
Everything was very good. Just as my previous stays have been

Reviewed on Oct 26, 2025

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
$127 nightly
The price is $149 total per night from Nov 16 to Nov 17
$149 total
Nov 16 - Nov 17
Total with taxes and fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (5,175 reviews)
Breakfast was organized and clean. Room was spacious

Reviewed on Oct 31, 2025

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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