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

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Cheap Flights from TPA to MDW starting at $98 One Way, $195 Round Trip

Prices starting at $195 for return flights and $98 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, Jan 27 - Sat, Jan 30
TPA
Tampa
MDW
Chicago
$195 Roundtrip, found 14 hours ago
$195
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Wed, Jan 27 from Tampa to Chicago, returning Sat, Jan 30, priced at $195 found 14 hours ago
Wed, Nov 11 - Sat, Nov 14
TPA
Tampa
MDW
Chicago
$198 Roundtrip, found 2 hours ago
$198
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Nov 11 from Tampa to Chicago, returning Sat, Nov 14, priced at $198 found 2 hours ago
Sat, Oct 24 - Thu, Oct 29
TPA
Tampa
MDW
Chicago
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Oct 24 from Tampa to Chicago, returning Thu, Oct 29, priced at $200 found 1 day ago
Tue, Oct 27 - Thu, Oct 29
TPA
Tampa
MDW
Chicago
$203 Roundtrip, found 2 days ago
$203
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Oct 27 from Tampa to Chicago, returning Thu, Oct 29, priced at $203 found 2 days ago
Thu, Oct 22 - Thu, Oct 29
TPA
Tampa
MDW
Chicago
$208 Roundtrip, found 1 day ago
$208
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Oct 22 from Tampa to Chicago, returning Thu, Oct 29, priced at $208 found 1 day 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
The price is $311 total per night from Oct 23 to Oct 24
$311 total
per night
Oct 23 - Oct 24
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 ...
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
The price is $255 total per night from Oct 25 to Oct 26
$255 total
per night
Oct 25 - Oct 26
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 ...
Holiday Inn & Suites Chicago - Downtown by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is $181 total per night from Oct 26 to Oct 27
$181 total
per night
Oct 26 - Oct 27
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! (10,221 reviews)
"The hotel is part of the original city architecture, so it is quite old. Taking that into consideration, some modern updates are in order. The building has central cooling and heat and you have control of the fan. So, you are at the mercy of whoever makes the hot/cold decision. We woke up to a freezing ..."

Reviewed on Sep 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

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is $221 total per night from Sep 27 to Sep 28
$221 total
per night
Sep 27 - Sep 28
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is $181 total per night from Oct 26 to Oct 27
$181 total
per night
Oct 26 - Oct 27
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! (10,221 reviews)
"The hotel is part of the original city architecture, so it is quite old. Taking that into consideration, some modern updates are in order. The building has central cooling and heat and you have control of the fan. So, you are at the mercy of whoever makes the hot/cold decision. We woke up to a freezing ..."

Reviewed on Sep 25, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
The price is $159 total per night from Sep 27 to Sep 28
$159 total
per night
Sep 27 - Sep 28
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 ...
8/10 Very Good! (2,341 reviews)
"Loved my stay the staff was nice and the location was great."

Reviewed on Sep 25, 2026

The Chicago Hotel Collection Ambassador Gold Coast
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
The price is $70 total per night from Oct 26 to Oct 27
$70 total
per night
Oct 26 - Oct 27
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 ...
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
The price is $110 total per night from Oct 18 to Oct 19
$110 total
per night
Oct 18 - Oct 19
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 ...
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
The price is $113 total per night from Oct 4 to Oct 5
$113 total
per night
Oct 4 - Oct 5
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 ...
7.8/10 Good! (3,194 reviews)
"Limpieza y amabilidad desayunos"

Reviewed on Sep 25, 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 $225 total per night from Sep 27 to Sep 28
$225 total
per night
Sep 27 - Sep 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. ...
7.8/10 Good! (3,388 reviews)
"Clean room, great staff, FANTASTIC location!"

Reviewed on Sep 24, 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 $189 total per night from Oct 25 to Oct 26
$189 total
per night
Oct 25 - Oct 26
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 ...
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 $70 total per night from Oct 26 to Oct 27
$70 total
per night
Oct 26 - Oct 27
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 ...
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
The price is $280 total per night from Oct 25 to Oct 26
$280 total
per night
Oct 25 - Oct 26
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 ...
8.4/10 Very Good! (3,023 reviews)
"The rooms were very clean and all the staff extremely helpful. The rooms are in need of updating. My bathroom had rust by the tub faucet, some peeling wallpaper. Overall a 4"

Reviewed on Sep 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
The price is $327 total per night from Oct 25 to Oct 26
$327 total
per night
Oct 25 - Oct 26
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! (2,671 reviews)
"Historic Palmer House does not disappoint. Rooms are small, but who cares when you can hang out in that beautiful lobby!"

Reviewed on Sep 24, 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
The price is $241 total per night from Sep 27 to Sep 28
$241 total
per night
Sep 27 - Sep 28
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! (5,986 reviews)
"This was our second stay at a Hilton property in 2026 (Phoenix, Milwaukee). Second time we had difficulties getting our room made up ... before 4:30p ... on extended stays. Vacationers like to sleep in. If your DND is on your door early, too bad, they don't come back. Chgo River North offered plenty ..."

Reviewed on Sep 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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