Cheap Flights to Lakeland - Winter Haven from $29
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How Much Does it Cost To Fly To Lakeland - Winter Haven?
The cheapest prices found with in the last 7 days for return flights were $58 and $29 for one-way flights to Lakeland - Winter Haven for the period specified. Prices and availability are subject to change. Additional terms apply
LGA
LaGuardia
MCO
Orlando Intl.
$58 Roundtrip, just found
$58
Roundtrip
just found
HPN
Westchester County
MCO
Orlando Intl.
$93 Roundtrip, found 2 hours ago
$93
Roundtrip
found 2 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| SJU | Tampa | February 12 to February 20 | $139 |
| SEA | Orlando | February 21 to February 28 | $148 |
| SJU | Orlando | February 7 to February 10 | $152 |
| SEA | Tampa | January 18 to January 30 | $159 |
| MQT | Tampa | January 31 to February 10 | $214 |
| ECP | Tampa | February 4 to February 6 | $263 |
| MQT | Orlando | January 6 to January 12 | $282 |
| SEA | Sarasota | January 12 to January 16 | $319 |
| ECP | Orlando | January 28 to February 4 | $321 |
| SJU | Sarasota | February 27 to March 7 | $347 |
| MQT | Sarasota | March 6 to March 25 | $359 |
| IMT | Orlando | January 28 to February 10 | $454 |
| ECP | Vero Beach | February 12 to February 15 | $628 |
| ECP | Melbourne | December 29 to December 30 | $682 |
| ADD | Tampa | January 3 to January 31 | $2,395 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| SJU | Tampa | December 26 to December 29 | $234 |
| SJU | Orlando | December 26 to December 31 | $274 |
| ECP | Orlando | December 28 to January 13 | $407 |
| PAE | Orlando | December 26 to January 5 | $545 |
| SEA | Tampa | December 26 to December 29 | $554 |
| SEA | Sarasota | December 26 to January 9 | $1,085 |
| IMT | Orlando | December 26 to January 2 | $1,521 |
| ADD | Tampa | December 27 to January 3 | $2,574 |
Lakeland - Winter Haven Flight Information
Traveling to | Lakeland - Winter Haven |
|---|---|
Lowest Price | $58 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines, Breeze Airways |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing Lakeland - Winter Haven Accommodation Deals
Howard Johnson by Wyndham Winter Haven FL
1300 3rd St Winter Haven FL
$85 nightly
The price is $95 total per night from Jan 18 to Jan 19
$95 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
Stay at this motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.8/10 (1,014 reviews)
A very curious staff! Which was very nice! We had a good time! The hotel was nice!Will definitely use them again!
Reviewed on Dec 14, 2025
Lakeland Hotel
3260 US Highway 98 N Lakeland FL
$129 nightly
The price is $144 total per night from Dec 21 to Dec 22
$144 total
Dec 21 - Dec 22
Total with taxes and fees
Book a stay at this business-friendly hotel in Lakeland. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff and the clean ...
6/10 (1,000 reviews)
Great time listening to tooners doing piorettes next door
Reviewed on Sep 2, 2025
Budget Inn Winter Haven
401 6th Street HWY 17N Winter Haven FL
$83 nightly
The price is $93 total per night from Dec 20 to Dec 21
$93 total
Dec 20 - Dec 21
Total with taxes and fees
Stay at this motel in Winter Haven. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions LEGOLAND® Florida and Winter Haven Public Library ...
6.6/10 (269 reviews)
Friendly professional
Reviewed on Nov 14, 2025
Save an average of 15% on thousands of hotels when you're signed in
Clarion Pointe Lakeland I-4
4321 Lakeland Park Dr Lakeland FL
$86 nightly
The price is $96 total per night from Dec 21 to Dec 22
$96 total
Dec 21 - Dec 22
Total with taxes and fees
Book a stay at this business-friendly hotel in Lakeland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,000 reviews)
Very comfortable room.clean.
Reviewed on Dec 9, 2025
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.
Luxury Hotels in Lakeland - Winter Haven
The Terrace Hotel Lakeland, Tapestry Collection by Hilton
329 E Main St Lakeland FL
$122 nightly
The price is $137 total per night from Dec 28 to Dec 29
$137 total
Dec 28 - Dec 29
Total with taxes and fees
Book a stay at this historic hotel in Lakeland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff in ...
9.2/10 Wonderful! (351 reviews)
Everything! We will be back every visit to Lakeland. We love this hotel,
Reviewed on Dec 5, 2025
Howard Johnson by Wyndham Winter Haven FL
1300 3rd St Winter Haven FL
$85 nightly
The price is $95 total per night from Jan 18 to Jan 19
$95 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
Stay at this motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.8/10 (1,014 reviews)
A very curious staff! Which was very nice! We had a good time! The hotel was nice!Will definitely use them again!
Reviewed on Dec 14, 2025
Budget Inn
530 South Scenic Highway Lake Wales FL
$70 nightly
The price is $78 total per night from Dec 20 to Dec 21
$78 total
Dec 20 - Dec 21
Total with taxes and fees
Stay at this motel in Lake Wales. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8.4/10 Very Good! (685 reviews)
Clean Room away from major traffic
Reviewed on Dec 15, 2025
Save an average of 15% on thousands of hotels when you're signed in
Baymont by Wyndham Lakeland
4375 Lakeland Park Dr Lakeland FL
$57 nightly
The price is $64 total per night from Dec 28 to Dec 29
$64 total
Dec 28 - Dec 29
Total with taxes and fees
Book a stay at this business-friendly hotel in Lakeland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
4.6/10 (1,004 reviews)
They were graceful helpful
Reviewed on Dec 7, 2025
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 Lakeland - Winter Haven
Extended Stay America Premier Suites Lakeland I4
4360 Lakeland Park Drive Lakeland FL
$81 nightly
The price is $90 total per night from Dec 25 to Dec 26
$90 total
Dec 25 - Dec 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Lakeland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.6/10 Good! (1,003 reviews)
Room was clean and front desk was nice
Reviewed on Dec 15, 2025
Howard Johnson by Wyndham Winter Haven FL
1300 3rd St Winter Haven FL
$85 nightly
The price is $95 total per night from Jan 18 to Jan 19
$95 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
Stay at this motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.8/10 (1,014 reviews)
A very curious staff! Which was very nice! We had a good time! The hotel was nice!Will definitely use them again!
Reviewed on Dec 14, 2025
The Terrace Hotel Lakeland, Tapestry Collection by Hilton
329 E Main St Lakeland FL
$122 nightly
The price is $137 total per night from Dec 28 to Dec 29
$137 total
Dec 28 - Dec 29
Total with taxes and fees
Book a stay at this historic hotel in Lakeland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff in ...
9.2/10 Wonderful! (351 reviews)
Everything! We will be back every visit to Lakeland. We love this hotel,
Reviewed on Dec 5, 2025
Save an average of 15% on thousands of hotels when you're signed in
Hampton Inn & Suites Lake Wales
22900 Hwy 27 Lake Wales FL
$130 nightly
The price is $145 total per night from Dec 25 to Dec 26
$145 total
Dec 25 - Dec 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Lake Wales. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Eagle ...
8.8/10 Excellent! (1,001 reviews)
Was very good. I am hoping for only a one night stay
Reviewed on Dec 17, 2025
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.
Best Lakeland - Winter Haven Flight and Hotel Packages
Lakeland - Winter Haven flight + hotel packages - economy flights
Price found within the past 48 hours. Click for updated prices.
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View all tripsLakeland - Winter Haven flight + hotel packages - premium economy flights
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Price found within the past 48 hours. Click for updated prices.
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See all available trips from Chicago to Lakeland - Winter Haven
View all tripsNeed a Car For After Your Flight?
Standard
Tampa, Florida, USA
$10
$42 total
found 8 hours ago
Fullsize
Tampa, Florida, USA
$13
$48 total
found 8 hours ago
Compact
Tampa, Florida, USA
$17
$36 total
found 1 day ago
Midsize
Tampa, Florida, USA
$17
$36 total
found 1 day ago
Lowest prices found within the past 8 hours. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
Plane Tickets To Lakeland - Winter Haven
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When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Lakeland - Winter Haven to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Lakeland - Winter Haven without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Lakeland - Winter Haven with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Lakeland - Winter Haven today!
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