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

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Cheap Flights from TPA to MDW starting at $97 One Way, $198 Round Trip

Prices starting at $198 for return flights and $97 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.

Sat, Jul 18 - Tue, Jul 21
TPA
Tampa
MDW
Chicago
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Jul 18 from Tampa to Chicago, returning Tue, Jul 21, priced at $198 found 1 day ago
Sat, Oct 17 - Sat, Oct 31
TPA
Tampa
MDW
Chicago
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Oct 17 from Tampa to Chicago, returning Sat, Oct 31, priced at $199 found 1 day ago
Tue, Oct 20 - Thu, Oct 22
TPA
Tampa
MDW
Chicago
$200 Roundtrip, found 2 days ago
$200
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Oct 20 from Tampa to Chicago, returning Thu, Oct 22, priced at $200 found 2 days ago
Wed, Aug 5 - Sat, Aug 8
TPA
Tampa
MDW
Chicago
$202 Roundtrip, found 1 day ago
$202
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Aug 5 from Tampa to Chicago, returning Sat, Aug 8, priced at $202 found 1 day ago
Sat, Oct 17 - Sat, Oct 31
TPA
Tampa
MDW
Chicago
$203 Roundtrip, found 1 day ago
$203
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Oct 17 from Tampa to Chicago, returning Sat, Oct 31, priced at $203 found 1 day 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
$127 nightly
The price is $151 total per night from Jul 5 to Jul 6
$151 total
Jul 5 - Jul 6
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! (1,108 reviews)
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Reviewed on Jun 23, 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
$228 nightly
The price is $271 total per night from Jul 8 to Jul 9
$271 total
Jul 8 - Jul 9
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! (1,152 reviews)
"Very clean room. Plenty of space to roam around throughout the hotel. Nice sauna"

Reviewed on Jun 23, 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
$159 nightly
The price is $190 total per night from Jul 1 to Jul 2
$190 total
Jul 1 - Jul 2
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 ...
8.8/10 Excellent! (1,041 reviews)
"Great stay, very accommodating, convenient location!"

Reviewed on Jun 23, 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

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 29 to Jun 30
$162 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! (10,167 reviews)
"Room smelled a little like mold or sitting water although the floors were never and the room was clear overall. The shower had a lot of rust in it. Hotel does not offer parking and the garage they recommend is was already full."

Reviewed on Jun 23, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
$139 nightly
The price is $166 total per night from Jul 1 to Jul 2
$166 total
Jul 1 - Jul 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
9/10 Wonderful! (4,465 reviews)
"Great location, rooms and service"

Reviewed on Jun 23, 2026

Hilton Chicago/Magnificent Mile Suites
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$127 nightly
The price is $145 total per night from Jun 28 to Jun 29
$145 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! (2,721 reviews)
"Breakfast was great!"

Reviewed on Jun 22, 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 Jul 7 to Jul 8
$73 total
Jul 7 - Jul 8
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! (1,965 reviews)
"Room was smelling"

Reviewed on Jun 22, 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
$112 nightly
The price is $124 total per night from Jun 29 to Jun 30
$124 total
Jun 29 - Jun 30
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! (1,526 reviews)
"The room was clean and the staff were helpful. The pool was warm and clean. My family and I enjoyed our stay!"

Reviewed on Jun 23, 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
$100 nightly
The price is $115 total per night from Jun 29 to Jun 30
$115 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! (3,027 reviews)
"The property was clean. Breakfast is in the restaurant and had decent options. Water and coffee available all day. The shuttle is a bit weird in that you have to sign up for it. The shuttle is pretty fast for a pickup from the blue line."

Reviewed on Jun 22, 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
$143 nightly
The price is $170 total per night from Jul 5 to Jul 6
$170 total
Jul 5 - Jul 6
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! (3,117 reviews)
"Was a great location right in the heart of Chicago, very close to many great restaurants and easy to access the trains and public transportation."

Reviewed on Jun 23, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$123 nightly
The price is $147 total per night from Jul 5 to Jul 6
$147 total
Jul 5 - Jul 6
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! (2,642 reviews)
"Did not like the small toilet that was in the room...it was made for a midget"

Reviewed on Jun 22, 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 Jul 7 to Jul 8
$73 total
Jul 7 - Jul 8
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! (1,965 reviews)
"Room was smelling"

Reviewed on Jun 22, 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
$219 nightly
The price is $260 total per night from Jul 7 to Jul 8
$260 total
Jul 7 - Jul 8
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! (2,882 reviews)
"Poor housekeeping. Rooms were dingy. Food was sub par. Staff was not helpful and kind of snarky."

Reviewed on Jun 23, 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 1 to Jul 2
$248 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! (2,496 reviews)
"Prepaid parking through Expedia not honored at the hotel. Staff completely unhelpful in sorting this issue out. Forced to double pay for parking. Rooms dated with older furnishings. Beds old. Plumbing drained poorly. Location nice but otherwise I would not recommend."

Reviewed on Jun 22, 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
$147 nightly
The price is $175 total per night from Jul 5 to Jul 6
$175 total
Jul 5 - Jul 6
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! (5,994 reviews)
"Very nice suite hotel. Best breakfast of any hotel for free, including an omelet bar. My only suggestion would be to put a magnifying mirror in bathroom and more creamers for in room coffee maker. Two little creamers does not work for two people."

Reviewed on Jun 23, 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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