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

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Cheap Flights from TPA to MDW starting at $86 One Way, $185 Round Trip

Prices starting at $185 for return flights and $86 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.

Wed, Jul 1 - Wed, Jul 8
TPA
Tampa
MDW
Chicago
$185 Roundtrip, found 5 hours ago
$185
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Jul 1 from Tampa to Chicago, returning Wed, Jul 8, priced at $185 found 5 hours ago
Wed, Jul 1 - Wed, Jul 8
TPA
Tampa
MDW
Chicago
$191 Roundtrip, found 5 hours ago
$191
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Jul 1 from Tampa to Chicago, returning Wed, Jul 8, priced at $191 found 5 hours ago
Tue, Jun 23 - Tue, Jun 30
TPA
Tampa
MDW
Chicago
$194 Roundtrip, found 6 days ago
$194
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Jun 23 from Tampa to Chicago, returning Tue, Jun 30, priced at $194 found 6 days ago
Tue, Jun 30 - Tue, Jul 7
TPA
Tampa
MDW
Chicago
$194 Roundtrip, found 2 hours ago
$194
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Tue, Jun 30 from Tampa to Chicago, returning Tue, Jul 7, priced at $194 found 2 hours ago
Tue, Jun 30 - Tue, Jul 7
TPA
Tampa
MDW
Chicago
$195 Roundtrip, found 2 hours ago
$195
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Tue, Jun 30 from Tampa to Chicago, returning Tue, Jul 7, priced at $195 found 2 hours ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
$314 nightly
The price is $373 total per night from May 27 to May 28
$373 total
May 27 - May 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,084 reviews)
"Everything was great"

Reviewed on May 26, 2026

Hyatt Regency McCormick Place Chicago
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
$193 nightly
The price is $229 total per night from Jun 14 to Jun 15
$229 total
Jun 14 - Jun 15
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! (2,219 reviews)
"Excellent hotel. Good location near/in Greektown. Very clean. Comfy beds. Staff friendly. Parking was a hassle and expensive but Ubered everywhere after parking."

Reviewed on May 26, 2026

Crowne Plaza Chicago West Loop by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$135 nightly
The price is $161 total per night from May 27 to May 28
$161 total
May 27 - May 28
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! (10,141 reviews)
"Everything was perfect. Great customer service."

Reviewed on May 25, 2026

Congress Plaza Hotel
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
$135 nightly
The price is $161 total per night from May 27 to May 28
$161 total
May 27 - May 28
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! (10,141 reviews)
"Everything was perfect. Great customer service."

Reviewed on May 25, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$175 nightly
The price is $208 total per night from May 27 to May 28
$208 total
May 27 - May 28
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! (4,252 reviews)
"This hotel is amazing, Great location, super clean and stuff was kind, informative and very respectful! The breakfast was well organized considering the amount people served! Not a missing items at any moment! The rooftop bar was very pleasant place to sit and chill. Strongly recommended!!!"

Reviewed on May 26, 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
$154 nightly
The price is $183 total per night from May 27 to May 28
$183 total
May 27 - May 28
Total with taxes and fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,477 reviews)
"El staff es un poco malhumorado Cuando tienes preguntas, la mayoria. Los tickets de comida o drinks gratis en realidad son descuentos, tienes q pagar. Excepto por el desayuno, solo use una vez cada uno, no me agrado, sali afuera. Regrese todos los demas tickets al hacer checkout. Gracias"

Reviewed on May 26, 2026

The Chicago Hotel Collection - Magnificent Mile
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
$65 nightly
The price is $73 total per night from May 27 to May 28
$73 total
May 27 - May 28
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! (1,936 reviews)
"Pros: Free parking, fairly low price on short notice. Inside of room was clean enough, in decent enough repair, didn't smell bad or anything, plenty of space, large bed which was comfortable enough. Once there, staff seemed pleasant enough. Cons: When I called the hotel directly the evening I booked, ..."

Reviewed on May 26, 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
$102 nightly
The price is $113 total per night from May 28 to May 29
$113 total
May 28 - May 29
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 ...
7.6/10 Good! (1,444 reviews)
"Convenient to airport. Appreciated having the airport shuttle."

Reviewed on May 26, 2026

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
$104 nightly
The price is $120 total per night from May 27 to May 28
$120 total
May 27 - May 28
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! (3,010 reviews)
"They forgot to remind us about breakfast! We didn't eat!"

Reviewed on May 26, 2026

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
The price is $152 total per night from May 27 to May 28
$152 total
per night
May 27 - May 28
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! (3,026 reviews)
"Good staff clean good people"

Reviewed on May 25, 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 $127 total per night from May 27 to May 28
$127 total
per night
May 27 - May 28
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! (2,618 reviews)
"The people were nice. The property was in a perfect location."

Reviewed on May 26, 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 $73 total per night from May 27 to May 28
$73 total
per night
May 27 - May 28
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! (1,936 reviews)
"Pros: Free parking, fairly low price on short notice. Inside of room was clean enough, in decent enough repair, didn't smell bad or anything, plenty of space, large bed which was comfortable enough. Once there, staff seemed pleasant enough. Cons: When I called the hotel directly the evening I booked, ..."

Reviewed on May 26, 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
$194 nightly
The price is $230 total per night from May 27 to May 28
$230 total
May 27 - May 28
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! (2,856 reviews)
"The gentleman at the front desk was rude; however, it’s something that could be addressed by management."

Reviewed on May 25, 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
$307 nightly
The price is $365 total per night from Jun 21 to Jun 22
$365 total
Jun 21 - Jun 22
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! (2,455 reviews)
"Loved the historic architecture and interior. It's well maintained and the staff was very helpful. The location is great too."

Reviewed on May 26, 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
$209 nightly
The price is $248 total per night from May 27 to May 28
$248 total
May 27 - May 28
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! (5,952 reviews)
"The hotel is in an excellent location, close to everything, which made the stay very convenient and enjoyable. The rooms were very clean, spacious, and comfortable, and the entire hotel felt well maintained and beautiful. The staff was also very friendly and welcoming throughout the stay, which made ..."

Reviewed on May 25, 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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