Cheap flights from MDW to PIE (Midway Intl. to St. Petersburg-Clearwater Intl.)

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Hotel Ideas near St. Petersburg-Clearwater Intl.

Airport Hotels near St. Petersburg-Clearwater Intl.

Hilton St. Petersburg Carillon Park

Hilton St. Petersburg Carillon Park

3.5 out of 5
950 Lake Carillon Dr St. Petersburg FL
The price is $153 total per night from Dec 28 to Dec 29
$153 total
per night
Dec 28 - Dec 29
Book a stay at this business-friendly hotel in St. Petersburg. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
9/10 Wonderful! (1,005 reviews)
Everything was great, except the part of reserving the room Expedia offered me a bundle deal. I accepted it and before changing the hotel, I had gone on the chat with Expedia and they said I would still get the same deal because the whole hotel was cheaper and then they told me I had to cancel the ...

Reviewed on Dec 19, 2025

Hilton St. Petersburg Carillon Park
Days Inn by Wyndham Clearwater/Gulf to Bay

Days Inn by Wyndham Clearwater/Gulf to Bay

2 out of 5
2940 Gulf To Bay Blvd Clearwater FL
The price is $75 total per night from Dec 25 to Dec 26
$75 total
per night
Dec 25 - Dec 26
Stay at this hotel in Clearwater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7/10 Good! (1,144 reviews)
The parking was safe and close to our room, even though I passed the entrance several times. At check-in the desk attendant updated our room from the second floor to the bottom floor when she saw the difficulty my wife was having walking.

Reviewed on Dec 16, 2025

Days Inn by Wyndham Clearwater/Gulf to Bay
La Quinta Inn by Wyndham Clearwater Central

La Quinta Inn by Wyndham Clearwater Central

3 out of 5
Clearwater FL
The price is $114 total per night from Jan 4 to Jan 5
$114 total
per night
Jan 4 - Jan 5
Book a stay at this business-friendly hotel in Clearwater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
8.8/10 Excellent! (1,710 reviews)
All of the front staff are Excellent, especially the one with same Birthday as mine (Dec 10th) -- I forgot her name. The pool area and hot tub tucked away on the back are Grade A+. It could possibly be THEE BEST pool lounge chair I have ever has the pleasure of laying on. Breakfast is A++. They let ...

Reviewed on Dec 19, 2025

La Quinta Inn by Wyndham Clearwater Central
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 St. Petersburg

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
The price is $272 total per night from Jan 1 to Jan 2
$272 total
per night
Jan 1 - Jan 2
Book a stay at this beach hotel in Clearwater Beach. Enjoy a full-service spa, 3 restaurants, and a beach locale. Our guests praise the breakfast and the pool ...
9.4/10 Exceptional! (2,924 reviews)
Everything was great. We had an amazing time. We were there for a wedding. Totally enjoyed.

Reviewed on Dec 22, 2025

Wyndham Grand Clearwater Beach
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave Clearwater Beach FL
The price is $215 total per night from Jan 11 to Jan 12
$215 total
per night
Jan 11 - Jan 12
Book a stay at this beach resort in Clearwater Beach. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
8/10 Very Good! (2,363 reviews)
I will definitely be back❤️ it’s centered perfectly for the beach, night life, sport views and food amenities l

Reviewed on Dec 20, 2025

Hilton Clearwater Beach Resort & Spa
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
6000 Gulf Blvd St. Pete Beach FL
The price is $168 total per night from Jan 4 to Jan 5
$168 total
per night
Jan 4 - Jan 5
Book a stay at this beach resort in St. Pete Beach. Enjoy free WiFi, 4 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
8.2/10 Very Good! (1,543 reviews)
clean room and courteous check in

Reviewed on Dec 19, 2025

RumFish Beach at TradeWinds
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.

St. Petersburg Hotels With Airport Transportation

SureStay Hotel by Best Western St. Pete Clearwater Airport

SureStay Hotel by Best Western St. Pete Clearwater Airport

2.5 out of 5
Clearwater FL
The price is $84 total per night from Dec 24 to Dec 25
$84 total
per night
Dec 24 - Dec 25
Book a stay at this business-friendly hotel in Clearwater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,553 reviews)
provided great service

Reviewed on Dec 16, 2025

SureStay Hotel by Best Western St. Pete Clearwater Airport
La Quinta Inn & Suites by Wyndham St. Pete-Clearwater Airpt

La Quinta Inn & Suites by Wyndham St. Pete-Clearwater Airpt

3 out of 5
Clearwater FL
The price is $85 total per night from Dec 28 to Dec 29
$85 total
per night
Dec 28 - Dec 29
Book a stay at this business-friendly hotel in Clearwater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6/10 (1,006 reviews)
Everybody nice, good breakfast

Reviewed on Dec 20, 2025

La Quinta Inn & Suites by Wyndham St. Pete-Clearwater Airpt
Courtyard St. Petersburg Clearwater

Courtyard St. Petersburg Clearwater

3 out of 5
3131 Executive Dr Clearwater FL
The price is $157 total per night from Dec 24 to Dec 25
$157 total
per night
Dec 24 - Dec 25
Book a stay at this business-friendly hotel in Clearwater. Enjoy free parking, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
9/10 Wonderful! (998 reviews)
Smooth check in!

Reviewed on Dec 1, 2025

Courtyard St. Petersburg Clearwater
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 St. Petersburg Hotels

Rodeway Inn Clearwater - Central

Rodeway Inn Clearwater - Central

2 out of 5
21252 Us Highway 19 N Clearwater FL
The price is $64 total per night from Dec 30 to Dec 31
$64 total
per night
Dec 30 - Dec 31
Stay at this hotel in Clearwater. Enjoy free WiFi, free parking, and room service. Our guests praise the clean rooms in our reviews. Popular attractions Sand ...
5.2/10 (759 reviews)
parking was very easy and the staff was great .I would recomend this place to anyone . Very acomodating

Reviewed on Nov 17, 2025

Rodeway Inn Clearwater - Central
Budget Inn St Petersburg

Budget Inn St Petersburg

2 out of 5
800 34th Street N St. Petersburg FL
The price is $66 total per night from Dec 24 to Dec 25
$66 total
per night
Dec 24 - Dec 25
Stay at this hotel in St. Petersburg. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...
5.6/10 (1,003 reviews)
Great for the prices, great daytime staff

Reviewed on Dec 2, 2025

Budget Inn St Petersburg
Clearwater Beach Hotel

Clearwater Beach Hotel

2 out of 5
504 S. Gulfview Blvd. Clearwater Beach FL
The price is $127 total per night from Dec 24 to Dec 25
$127 total
per night
Dec 24 - Dec 25
Book a stay at this business-friendly hotel in Clearwater Beach. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the pool and ...
7.8/10 Good! (1,423 reviews)
clean room great service

Reviewed on Dec 19, 2025

Clearwater Beach 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.

Family Friendly Hotels in St. Petersburg

Alden Suites - A Beachfront Resort

Alden Suites - A Beachfront Resort

2.5 out of 5
5900 Gulf Blvd St. Pete Beach FL
Book a stay at this beach hotel in St. Pete Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions John's Pass Village & Boardwalk and ...
8.6/10 Excellent! (1,000 reviews)
Best experience ever will definitely be back great family trip

Reviewed on Feb 20, 2023

Alden Suites - A Beachfront Resort
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
5500 Gulf Blvd St. Pete Beach FL
The price is $179 total per night from Jan 4 to Jan 5
$179 total
per night
Jan 4 - Jan 5
Book a stay at this beach resort in St. Pete Beach. Enjoy free WiFi, 5 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
7.2/10 Good! (1,001 reviews)

Families like: Outdoor pools, waterslide, kids club, miniature golf

Travelers say...
We didn't have a bar, and didn't check for pots and pans

Reviewed on Dec 15, 2025

Island Grand at TradeWinds
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
10700 Gulf Blvd Treasure Island FL
Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the bar in our reviews. ...
8.6/10 Excellent! (1,002 reviews)
One of my favorite beaches. Live bands and tiki bar are epic.

Reviewed on Nov 20, 2024

Thunderbird Beach Resort
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.

MDW to PIE Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
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
PIE Address & GPS
Address:
Suite 221 - Terminal Building
Saint Petersburg FL, 33762
United States
IATA Code:
PIE
Longitude:
-82.695109
Latitude:
27.912005
Time Zone:
America/New_York

Frequently asked questions

What airlines have the most flights from Chicago Airport to St. Pete-Clearwater Intl. Airport?
You'll have to make at least one stopover if you're flying from MDW to St. Pete-Clearwater Intl. Airport. For now, there are no airlines that offer direct flights on this route.

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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