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

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Cheap Flights from TPA to MDW starting at $87 One Way, $197 Round Trip

Prices starting at $197 for return flights and $87 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, Sep 2 - Tue, Sep 8
TPA
Tampa
MDW
Chicago
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 2 from Tampa to Chicago, returning Tue, Sep 8, priced at $197 found 1 day ago
Wed, Aug 5 - Mon, Aug 10
TPA
Tampa
MDW
Chicago
$200 Roundtrip, found 3 days ago
$200
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Aug 5 from Tampa to Chicago, returning Mon, Aug 10, priced at $200 found 3 days ago
Thu, Oct 1 - Mon, Oct 5
TPA
Tampa
MDW
Chicago
$203 Roundtrip, found 2 days ago
$203
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Oct 1 from Tampa to Chicago, returning Mon, Oct 5, priced at $203 found 2 days ago
Sat, Sep 5 - Tue, Sep 8
TPA
Tampa
MDW
Chicago
$208 Roundtrip, found 2 days ago
$208
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Tampa to Chicago, returning Tue, Sep 8, priced at $208 found 2 days ago
Thu, Oct 1 - Mon, Oct 5
TPA
Tampa
MDW
Chicago
$209 Roundtrip, found 2 days ago
$209
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Oct 1 from Tampa to Chicago, returning Mon, Oct 5, priced at $209 found 2 days 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
$207 nightly
The price is $246 total per night from Jul 1 to Jul 2
$246 total
Jul 1 - Jul 2
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! (1,088 reviews)
"Great experience! The room was clean and he staff were lovely"

Reviewed on May 31, 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
$170 nightly
The price is $202 total per night from Jun 29 to Jun 30
$202 total
Jun 29 - Jun 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! (2,228 reviews)
"N/a"

Reviewed on May 30, 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
$155 nightly
The price is $184 total per night from Jun 29 to Jun 30
$184 total
Jun 29 - Jun 30
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! (10,134 reviews)
"The room was small and was missing modern convinces-microwave-better seating space. The staff were friendly and the restaurant was great! I only wished we had gotten a better room! Special shout out to Steve P. the doorman for his service and friendly demeanor!!"

Reviewed on May 30, 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
$155 nightly
The price is $184 total per night from Jun 29 to Jun 30
$184 total
Jun 29 - Jun 30
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! (10,134 reviews)
"The room was small and was missing modern convinces-microwave-better seating space. The staff were friendly and the restaurant was great! I only wished we had gotten a better room! Special shout out to Steve P. the doorman for his service and friendly demeanor!!"

Reviewed on May 30, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$203 nightly
The price is $242 total per night from Jun 30 to Jul 1
$242 total
Jun 30 - Jul 1
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! (4,301 reviews)
"Clean"

Reviewed on May 31, 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 Jun 14 to Jun 15
$183 total
Jun 14 - Jun 15
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! (1,493 reviews)
"Asked for a room with a tub didn't get it and got extra charges after stay. Got my full deposit back but got extra charges. And paid for breakfast after being told it was included. No cable on tv"

Reviewed on May 30, 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 Jun 10 to Jun 11
$73 total
Jun 10 - Jun 11
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! (1,940 reviews)
"She was very helpful n super kind love the stay"

Reviewed on May 30, 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 Jun 21 to Jun 22
$113 total
Jun 21 - Jun 22
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! (1,456 reviews)
"OverLl good trip"

Reviewed on May 30, 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
$119 nightly
The price is $137 total per night from Jun 1 to Jun 2
$137 total
Jun 1 - Jun 2
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! (3,003 reviews)
"Convenient 24 hour shuttle service to airport. Great pizza restaurant in Lobby. The property feels very old and not in good condition (ripped sofa, bad paint job, and smoke detector beeping every 30 seconds due to low battery that were not replaced despite asking). Feels like a cheap roadside ..."

Reviewed on May 29, 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
$137 nightly
The price is $163 total per night from Jun 29 to Jun 30
$163 total
Jun 29 - Jun 30
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. ...
8/10 Very Good! (3,040 reviews)
"Overall, we had a good stay at the Freehand Chicago. The location was convenient, and despite being in a busy area, we slept peacefully throughout the night. The hotel was also accommodating in holding our luggage after checkout since we had a later flight, which we appreciated. That said, there ..."

Reviewed on May 30, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$128 nightly
The price is $152 total per night from Jul 1 to Jul 2
$152 total
Jul 1 - Jul 2
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! (2,612 reviews)
"Welcoming and friendly staff"

Reviewed on May 30, 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
$65 nightly
The price is $73 total per night from Jun 10 to Jun 11
$73 total
Jun 10 - Jun 11
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! (1,940 reviews)
"She was very helpful n super kind love the stay"

Reviewed on May 30, 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
$245 nightly
The price is $291 total per night from Jun 28 to Jun 29
$291 total
Jun 28 - Jun 29
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! (2,858 reviews)
"Always love staying at the embassy one of my fav hotels. Although 2 out of the 4 elevators are under maintenance so it was a bit of a wait to get one. Also the bathroom does need a bit of tlc. But overall it was a great stay staff was friendly and did offer parking but at 65 a night but it is ..."

Reviewed on May 30, 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
$218 nightly
The price is $259 total per night from Jul 1 to Jul 2
$259 total
Jul 1 - Jul 2
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! (2,466 reviews)
"Step back into time. With modern amenities, a great gym, good food and proximity to the red line, this will be my go to hotel for baseball games"

Reviewed on May 30, 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
$220 nightly
The price is $261 total per night from Jun 14 to Jun 15
$261 total
Jun 14 - Jun 15
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! (5,955 reviews)
"The room needs to be deep cleaned badly. The carpet was filthy, so you could just see the dirt buildup on it. The bathtub was giving sleazy motel; rusted and peeling. The bathroom ceiling needs to be redone and checked for mold, expeditiously! The doors and some of the walls looked as though someone ..."

Reviewed on May 31, 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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