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

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Cheap Flights from TPA to MDW starting at $105 One Way, $209 Round Trip

Prices starting at $209 for return flights and $105 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, Jul 28 - Wed, Jul 29
TPA
Tampa
MDW
Chicago
$209 Roundtrip, found 4 days ago
$209
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Jul 28 from Tampa to Chicago, returning Wed, Jul 29, priced at $209 found 4 days ago
Tue, Jul 28 - Wed, Jul 29
TPA
Tampa
MDW
Chicago
$219 Roundtrip, found 4 days ago
$219
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Jul 28 from Tampa to Chicago, returning Wed, Jul 29, priced at $219 found 4 days ago
Tue, Oct 20 - Wed, Oct 21
TPA
Tampa
MDW
Chicago
$225 Roundtrip, found 6 days ago
$225
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Oct 20 from Tampa to Chicago, returning Wed, Oct 21, priced at $225 found 6 days ago
Wed, Sep 23 - Mon, Sep 28
TPA
Tampa
MDW
Chicago
$227 Roundtrip, found 3 days ago
$227
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Sep 23 from Tampa to Chicago, returning Mon, Sep 28, priced at $227 found 3 days ago
Tue, Sep 22 - Wed, Sep 23
TPA
Tampa
MDW
Chicago
$230 Roundtrip, found 1 hour ago
$230
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Sep 22 from Tampa to Chicago, returning Wed, Sep 23, priced at $230 found 1 hour 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
$203 nightly
The price is $241 total per night from Jul 2 to Jul 3
$241 total
Jul 2 - Jul 3
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! (1,112 reviews)
"Nice hotel..... convenient location. RUDE front desk staff that seemed irritated when asked about literally ANYTHING! The girl who checked us in was nice but after that it went downhill fast. Bell desk staff was great on the way out which helped us exit without being completely frustrates. Paying ..."

Reviewed on Jun 8, 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
$145 nightly
The price is $172 total per night from Jul 6 to Jul 7
$172 total
Jul 6 - Jul 7
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! (2,244 reviews)
"They were able to keep my luggage while i wait for my from to be ready and provided food and beverage"

Reviewed on Jun 8, 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
$136 nightly
The price is $162 total per night from Jun 30 to Jul 1
$162 total
Jun 30 - Jul 1
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! (10,212 reviews)
"Cool hotel, good history"

Reviewed on Jun 8, 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
$136 nightly
The price is $162 total per night from Jun 30 to Jul 1
$162 total
Jun 30 - Jul 1
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! (10,212 reviews)
"Cool hotel, good history"

Reviewed on Jun 8, 2026

Congress Plaza Hotel
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 28 to Jun 29
$183 total
Jun 28 - Jun 29
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! (1,539 reviews)
"They were awesome to clean our room before we checked out . Which we checked out 2 days later"

Reviewed on Jun 8, 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$135 nightly
The price is $154 total per night from Jun 28 to Jun 29
$154 total
Jun 28 - Jun 29
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,633 reviews)
"The room was very nice and clean. The staff was very helpful and accommodating. There was a buffet breakfast which had a variety of food and fruit. You could also get an omelette made to order. I did not experience the bar so I can not speak on it. I did order some takeout from the bar restaurant. ..."

Reviewed on Jun 8, 2026

Hyatt Regency O'Hare 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
$65 nightly
The price is $73 total per night from Jun 29 to Jun 30
$73 total
Jun 29 - Jun 30
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! (1,952 reviews)
"For a simple stay, this place fits the bill. The staff was awesome. The area doesn’t have much but a Subway Sandwich shop that’s open til 11pm on Sundays, which was a plus for me, so plan on renting a car or grabbing a ride share for all of your activities."

Reviewed on Jun 3, 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 $106 total per night from Jun 30 to Jul 1
$106 total
Jun 30 - Jul 1
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! (1,487 reviews)
"No stars. Filthy everywhere. Pool area was not sanitary. Food was disgusting. So few tables you couldn’t get in if you wanted to. Bathroom was ok but the tub filled with water when showering and there were no towel bars or even holes where they once were. So they fell to the floor. Room was equally ..."

Reviewed on Jun 8, 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
$101 nightly
The price is $116 total per night from Jun 29 to Jun 30
$116 total
Jun 29 - Jun 30
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! (3,043 reviews)
"Receptionist to check in was wonderful."

Reviewed on Jun 8, 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
$130 nightly
The price is $154 total per night from Jul 8 to Jul 9
$154 total
Jul 8 - Jul 9
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! (3,080 reviews)
"Cool architecture, great location easy to walk everywhere. Room could have been cleaner. Staff could have been friendlier."

Reviewed on Jun 8, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$134 nightly
The price is $159 total per night from Jun 29 to Jun 30
$159 total
Jun 29 - Jun 30
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! (2,616 reviews)
"Get the job done for a quick stay. Could not offer parking recommendations, so do your own research if coming with a rental. Centrally located. Friendly staff."

Reviewed on Jun 8, 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 29 to Jun 30
$73 total
Jun 29 - Jun 30
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! (1,952 reviews)
"For a simple stay, this place fits the bill. The staff was awesome. The area doesn’t have much but a Subway Sandwich shop that’s open til 11pm on Sundays, which was a plus for me, so plan on renting a car or grabbing a ride share for all of your activities."

Reviewed on Jun 3, 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
$244 nightly
The price is $290 total per night from Jul 1 to Jul 2
$290 total
Jul 1 - Jul 2
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! (2,879 reviews)
"Everything was fantastic food, happy hour, check in staff and bag holding staff. Housekeeping was good but they need to really clean shower tile"

Reviewed on Jun 8, 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
$209 nightly
The price is $248 total per night from Jul 2 to Jul 3
$248 total
Jul 2 - Jul 3
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! (2,486 reviews)
"The breakfast was good. Room was comfortable. Could of used a coffee maker in the room. Still waiting for a receipt for my stay"

Reviewed on Jun 8, 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
$211 nightly
The price is $250 total per night from Jul 6 to Jul 7
$250 total
Jul 6 - Jul 7
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! (5,968 reviews)
"Breakfast every morning and drinks every night were amazing!"

Reviewed on Jun 8, 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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