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 2 days ago
$197
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Sep 2 from Tampa to Chicago, returning Tue, Sep 8, priced at $197 found 2 days ago
Wed, Aug 5 - Mon, Aug 10
TPA
Tampa
MDW
Chicago
$200 Roundtrip, found 4 days ago
$200
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Aug 5 from Tampa to Chicago, returning Mon, Aug 10, priced at $200 found 4 days ago
Thu, Oct 1 - Mon, Oct 5
TPA
Tampa
MDW
Chicago
$203 Roundtrip, found 3 days ago
$203
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Oct 1 from Tampa to Chicago, returning Mon, Oct 5, priced at $203 found 3 days ago
Sat, Sep 5 - Tue, Sep 8
TPA
Tampa
MDW
Chicago
$208 Roundtrip, found 3 days ago
$208
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Tampa to Chicago, returning Tue, Sep 8, priced at $208 found 3 days ago
Thu, Oct 1 - Mon, Oct 5
TPA
Tampa
MDW
Chicago
$209 Roundtrip, found 3 days ago
$209
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Oct 1 from Tampa to Chicago, returning Mon, Oct 5, priced at $209 found 3 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
$215 nightly
The price is $255 total per night from Jul 2 to Jul 3
$255 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! (1,091 reviews)
"Really hood"

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! (2,232 reviews)
"It was a relaxing stay"

Reviewed on Jun 1, 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! (10,141 reviews)
"No heat, toilet was broken, no hot water. I left. Front staff was very rude. The staff who came to fix the toilet and bring me more blankets and a portable heater were very nice."

Reviewed on May 31, 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! (10,141 reviews)
"No heat, toilet was broken, no hot water. I left. Front staff was very rude. The staff who came to fix the toilet and bring me more blankets and a portable heater were very nice."

Reviewed on May 31, 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! (1,497 reviews)
"Everything was great"

Reviewed on May 31, 2026

The Chicago Hotel Collection - Magnificent Mile
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! (4,308 reviews)
"Great location, excellent service, very clean. I will definitely stay there on next visit"

Reviewed on Jun 1, 2026

Hotel Riu Plaza 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 23 to Jun 24
$73 total
Jun 23 - Jun 24
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! (1,944 reviews)
"The floor felt like I was going to fall through. My feet turned black from dirty floor. Doors looked like they had been water damage. The top bed blanket was dirty. For the price I paid, should of had a mIcrowave and refrigerator included."

Reviewed on Jun 1, 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
$103 nightly
The price is $114 total per night from Jun 21 to Jun 22
$114 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! (1,459 reviews)
"Overall good experience and stuff very nice and helpful."

Reviewed on May 31, 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
$139 nightly
The price is $160 total per night from Jun 2 to Jun 3
$160 total
Jun 2 - Jun 3
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! (3,009 reviews)
"It is not a fancy hotel and could use some repair (notably elevators). Nice having the Pizzeria Uno in the lobby. I paid for parking but their lot was full every night, but I never had trouble finding free places to park on the street. It was a very affordable hotel so was sufficient for my ..."

Reviewed on Jun 1, 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! (3,043 reviews)
"Great price, the bunk beds were fun!"

Reviewed on Jun 1, 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! (2,614 reviews)
"The room was clean although pretty outdated. The staff was helpful and polite."

Reviewed on May 31, 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 23 to Jun 24
$73 total
Jun 23 - Jun 24
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! (1,944 reviews)
"The floor felt like I was going to fall through. My feet turned black from dirty floor. Doors looked like they had been water damage. The top bed blanket was dirty. For the price I paid, should of had a mIcrowave and refrigerator included."

Reviewed on Jun 1, 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! (2,860 reviews)
"Excelent stay in Chicago with a great breakfast that is include. Awesome location and staff was very helpful."

Reviewed on May 31, 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! (2,469 reviews)
"This is the second and the last time I stay at the Palmer. I like the proximity to certain landmarks and the beds were comfy but other than that, the bathroom wasn't clean, there was a lot of hair in the tub, the shower faucet handle was filled with black scum on the inside. There was also a piece ..."

Reviewed on May 31, 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! (5,959 reviews)
"Brkfat just ok Stakl resonanle Location great Bar not so great"

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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