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

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Cheap Flights from TPA to MDW starting at $49 One Way, $98 Round Trip

Prices starting at $98 for return flights and $49 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.

Tue, Jan 13 - Tue, Jan 20
TPA
Tampa
MDW
Chicago
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jan 13 from Tampa to Chicago, returning Tue, Jan 20, priced at $98 found 1 day ago
Thu, Jan 22 - Mon, Jan 26
TPA
Tampa
MDW
Chicago
$99 Roundtrip, found 4 days ago
$99
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Jan 22 from Tampa to Chicago, returning Mon, Jan 26, priced at $99 found 4 days ago
Tue, Jan 20 - Sat, Jan 31
TPA
Tampa
MDW
Chicago
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jan 20 from Tampa to Chicago, returning Sat, Jan 31, priced at $108 found 1 day ago
Thu, Jan 22 - Mon, Jan 26
TPA
Tampa
MDW
Chicago
$109 Roundtrip, found 6 days ago
$109
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Jan 22 from Tampa to Chicago, returning Mon, Jan 26, priced at $109 found 6 days ago
Fri, Jan 30 - Mon, Feb 2
TPA
Tampa
MDW
Chicago
$125 Roundtrip, found 6 days ago
$125
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, Jan 30 from Tampa to Chicago, returning Mon, Feb 2, priced at $125 found 6 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
$91 nightly
The price is $107 total per night from Dec 22 to Dec 23
$107 total
Dec 22 - Dec 23
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 ...
8.8/10 Excellent! (1,761 reviews)
Location it's the best from this hotel close to the Fulton Market. David in the restaurant area it's very friendly and makes you feel at home. Hotel staff in general are very nice.

Reviewed on Dec 15, 2025

Crowne Plaza Chicago West Loop by IHG
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
59 E. 11th Street Chicago IL
$81 nightly
The price is $95 total per night from Jan 5 to Jan 6
$95 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
8.6/10 Excellent! (2,147 reviews)
Clean room, nice building and location. Staff was amazing as well and got me out of a meeting crunch by helping me print.

Reviewed on Dec 16, 2025

Homewood Suites by Hilton Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
$73 nightly
The price is $86 total per night from Jan 5 to Jan 6
$86 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Book a stay at this 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! (1,756 reviews)
clean room, close to food places, walkable & best part was no loud noise

Reviewed on Dec 12, 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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
$81 nightly
The price is $95 total per night from Jan 6 to Jan 7
$95 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (3,467 reviews)
I was allowed to check in early. Pleasant front desk staff. Nice room.

Reviewed on Dec 12, 2025

Hilton Chicago/Magnificent Mile Suites
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
$127 nightly
The price is $149 total per night from Jan 4 to Jan 5
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
9.2/10 Wonderful! (2,133 reviews)
The rooms were comfortable and spacious. The bed was comfortable. The vent up near the ceiling in my room needed to be cleaned. The shower was fantastic. Could have used instructions on how to use the coffee maker lol. The location was amazing! We hung out down in the lobby area and the staff were ...

Reviewed on Dec 16, 2025

Silversmith Hotel Chicago Downtown
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
$88 nightly
The price is $103 total per night from Dec 23 to Dec 24
$103 total
Dec 23 - Dec 24
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,995 reviews)
Great friendy staff, Smooth Check-in Check-out Process and the view from the room was just stunning.

Reviewed on Dec 16, 2025

Club Quarters Hotel Wacker at Michigan, 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
$45 nightly
The price is $51 total per night from Dec 28 to Dec 29
$51 total
Dec 28 - Dec 29
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! (1,719 reviews)
Parking was easy

Reviewed on Dec 8, 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 Jan 11 to Jan 12
$101 total
Jan 11 - Jan 12, 2026
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 ...
7.2/10 Good! (1,215 reviews)
Good service

Reviewed on Dec 14, 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
$67 nightly
The price is $77 total per night from Dec 30 to Dec 31
$77 total
Dec 30 - Dec 31
Total with taxes and fees
Book a stay at this 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! (2,768 reviews)
Good price and clean

Reviewed on Dec 14, 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
$64 nightly
The price is $76 total per night from Jan 5 to Jan 6
$76 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
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. ...
7.8/10 Good! (2,638 reviews)
The front desk eas very easy to deal with and helpful

Reviewed on Dec 9, 2025

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$77 nightly
The price is $90 total per night from Dec 21 to Dec 22
$90 total
Dec 21 - Dec 22
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 ...
7.4/10 Good! (2,488 reviews)
Clean room, highly walkable location and friendly staff

Reviewed on Dec 12, 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
$45 nightly
The price is $51 total per night from Dec 28 to Dec 29
$51 total
Dec 28 - Dec 29
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! (1,719 reviews)
Parking was easy

Reviewed on Dec 8, 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
$106 nightly
The price is $124 total per night from Jan 11 to Jan 12
$124 total
Jan 11 - Jan 12, 2026
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! (2,741 reviews)
Clean room and friendly staff, overall good stay

Reviewed on Dec 12, 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
$133 nightly
The price is $152 total per night from Dec 30 to Dec 31
$152 total
Dec 30 - Dec 31
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 ...
8.4/10 Very Good! (2,123 reviews)
A beautiful hotel! The atmosphere is stunning. It was stunningly decorated for Christmas. Staff was very helpful and friendly, the rooms were clean and comfy; great pillows. Food at the hotel was delicious. The location is excellent. Right by the L, close to Millennium Park, near great restaurants. ...

Reviewed on Dec 12, 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
$98 nightly
The price is $116 total per night from Jan 6 to Jan 7
$116 total
Jan 6 - Jan 7, 2026
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 ...
8.4/10 Very Good! (5,385 reviews)
Spacious rooms , free drinks and great breakfast

Reviewed on Dec 14, 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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