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

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Cheap Flights from TPA to MDW starting at $80 One Way, $173 Round Trip

Prices starting at $173 for return flights and $80 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.

Thu, Aug 6 - Tue, Aug 18
TPA
Tampa
MDW
Chicago
$173 Roundtrip, found 2 days ago
$173
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Aug 6 from Tampa to Chicago, returning Tue, Aug 18, priced at $173 found 2 days ago
Sat, Sep 5 - Tue, Sep 8
TPA
Tampa
MDW
Chicago
$193 Roundtrip, found 3 days ago
$193
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Tampa to Chicago, returning Tue, Sep 8, priced at $193 found 3 days ago
Thu, Aug 27 - Sat, Aug 29
TPA
Tampa
MDW
Chicago
$195 Roundtrip, found 2 days ago
$195
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Aug 27 from Tampa to Chicago, returning Sat, Aug 29, priced at $195 found 2 days ago
Sat, Sep 5 - Tue, Sep 8
TPA
Tampa
MDW
Chicago
$198 Roundtrip, found 3 days ago
$198
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Tampa to Chicago, returning Tue, Sep 8, priced at $198 found 3 days ago
Sat, Sep 5 - Tue, Sep 8
TPA
Tampa
MDW
Chicago
$200 Roundtrip, found 3 days ago
$200
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Tampa to Chicago, returning Tue, Sep 8, priced at $200 found 3 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Hotel Chicago West Loop, SureStay Collection by Best Western

Hotel Chicago West Loop, SureStay Collection by Best Western

2.5 out of 5
1622 W Jackson Blvd Chicago IL
$151 nightly
The price is $180 total per night from Jul 12 to Jul 13
$180 total
Jul 12 - Jul 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.2/10 Very Good! (1,125 reviews)
"The room was small but clean. The bed seemed smaller than a double but wasn't a big deal. The staff were very friendly and helpful. I was there to go to the University of Chicago hospital, which was very close by. The hotel parking is $25, however I parked in the lot next door for $11 all night."

Reviewed on Jul 9, 2026

Hotel Chicago West Loop, SureStay Collection by Best Western
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
$261 nightly
The price is $310 total per night from Aug 11 to Aug 12
$310 total
Aug 11 - Aug 12
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! (1,193 reviews)
"Like everything what was offered"

Reviewed on Jul 10, 2026

Hyatt Regency McCormick Place Chicago
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
$183 nightly
The price is $218 total per night from Aug 9 to Aug 10
$218 total
Aug 9 - Aug 10
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,066 reviews)
"We had a nice time! Clean room and luv the rooftop pool. Only down fall breakfast prices."

Reviewed on Jul 11, 2026

Holiday Inn & Suites Chicago - Downtown by IHG
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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$154 nightly
The price is $183 total per night from Jul 27 to Jul 28
$183 total
Jul 27 - Jul 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (1,732 reviews)
"It gets worse and worse every time we stay…"

Reviewed on Jul 10, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
$251 nightly
The price is $298 total per night from Jul 26 to Jul 27
$298 total
Jul 26 - Jul 27
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,903 reviews)
"Everything was nice and clean. Staff was very helpful."

Reviewed on Jul 11, 2026

Omni Chicago Hotel
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
$229 nightly
The price is $269 total per night from Aug 2 to Aug 3
$269 total
Aug 2 - Aug 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,339 reviews)
"Very nice"

Reviewed on Jul 11, 2026

Hilton 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.

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 Aug 3 to Aug 4
$73 total
Aug 3 - Aug 4
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! (1,982 reviews)
"Very bare bones,like a jail cell. No fridge, or microwave. First world problems I guess. Staff was nice and friendly, just room was very depressing. I had booked for several days, so was stuck. Bed good, clean. If you are looking for a cheap one nighter before flight, ok for that. Lot of road construction ..."

Reviewed on Jul 10, 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
$115 nightly
The price is $127 total per night from Jul 21 to Jul 22
$127 total
Jul 21 - Jul 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! (1,574 reviews)
"This place is absolutely horrible. So gross. You’re better off sleeping in your car. Everything was dirty and there were bugs in the room. We stayed for about 20 minutes before leaving. Do not stay here."

Reviewed on Jul 10, 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
$109 nightly
The price is $125 total per night from Jul 19 to Jul 20
$125 total
Jul 19 - Jul 20
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! (3,064 reviews)
"Room dirty bed is has little blood dirty I'm cancel my hotel thanks"

Reviewed on Jul 10, 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
$148 nightly
The price is $176 total per night from Aug 10 to Aug 11
$176 total
Aug 10 - Aug 11
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! (3,176 reviews)
"Nice hotel for the price. It was in the city - walkable to all city attractions. If you don’t mind staying in a room about the size of a cruise ship interior room then you will enjoy your stay. We enjoyed our stay because we spent most of the time out exploring the city."

Reviewed on Jul 10, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$157 nightly
The price is $186 total per night from Aug 10 to Aug 11
$186 total
Aug 10 - Aug 11
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 ...
7.6/10 Good! (2,693 reviews)
"The room that we got looked nothing like the photos on the website. The hotel looked like it might have been some sort of old school apartment building once: the hallways, the rooms, etc. all felt more like a cheap apartment building than a hotel. The room was surprisingly large, which was probably ..."

Reviewed on Jul 10, 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 Aug 3 to Aug 4
$73 total
Aug 3 - Aug 4
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! (1,982 reviews)
"Very bare bones,like a jail cell. No fridge, or microwave. First world problems I guess. Staff was nice and friendly, just room was very depressing. I had booked for several days, so was stuck. Bed good, clean. If you are looking for a cheap one nighter before flight, ok for that. Lot of road construction ..."

Reviewed on Jul 10, 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
$246 nightly
The price is $293 total per night from Aug 11 to Aug 12
$293 total
Aug 11 - Aug 12
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! (2,917 reviews)
"Clean and feels welcoming"

Reviewed on Jul 11, 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
$241 nightly
The price is $287 total per night from Aug 9 to Aug 10
$287 total
Aug 9 - Aug 10
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! (2,514 reviews)
"😘"

Reviewed on Jul 10, 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
$201 nightly
The price is $240 total per night from Jul 19 to Jul 20
$240 total
Jul 19 - Jul 20
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! (6,026 reviews)
"Very clean suite, even safe to use pull out couch! You may have to travel far to your room, but place is pretty quiet and worth the value! Very impressed with breakfast options. Parking was a little confusing, would be better to explain more on the website on best practices and where to get a luggage ..."

Reviewed on Jul 10, 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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