$44 Cheap flight deals from Chicago (CHI) to Lake Wales (TPA)

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This Weekend's Flight Deals from Chicago to Lake Wales

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Mar 1 - Thu, Mar 5
ORD
O'Hare Intl.
MCO
Orlando Intl.
$156 Roundtrip, found 1 hour ago
$156
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Mar 1 from O'Hare Intl. to Orlando Intl., returning Thu, Mar 5, priced at $156 found 1 hour ago
Sun, Mar 1 - Fri, Mar 6
MDW
Midway Intl.
MCO
Orlando Intl.
$165 Roundtrip, found 22 hours ago
$165
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Sun, Mar 1 from Midway Intl. to Orlando Intl., returning Fri, Mar 6, priced at $165 found 22 hours ago
Sun, Mar 1 - Tue, Mar 17
ORD
O'Hare Intl.
TPA
Tampa Intl.
$170 Roundtrip, found 2 hours ago
$170
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sun, Mar 1 from O'Hare Intl. to Tampa Intl., returning Tue, Mar 17, priced at $170 found 2 hours ago
Fri, Feb 27 - Sat, Feb 28
MDW
Midway Intl.
TPA
Tampa Intl.
$204 Roundtrip, found 6 hours ago
$204
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Fri, Feb 27 from Midway Intl. to Tampa Intl., returning Sat, Feb 28, priced at $204 found 6 hours ago

Airfares from $44 One Way, $68 Round Trip from Chicago to Lake Wales

Prices starting at $68 for return flights and $44 for one-way flights to Lake Wales were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Apr 20 - Sat, Apr 25
MDW
Chicago
MCO
Orlando
$68 Roundtrip, found 4 days ago
$68
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Apr 20 from Chicago to Orlando, returning Sat, Apr 25, priced at $68 found 4 days ago
Sat, Mar 7 - Tue, Mar 17
ORD
Chicago
MCO
Orlando
$81 Roundtrip, found 4 days ago
$81
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Mar 7 from Chicago to Orlando, returning Tue, Mar 17, priced at $81 found 4 days ago
Sat, May 9 - Sat, May 16
ORD
Chicago
TPA
Tampa
$87 Roundtrip, found 6 hours ago
$87
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, May 9 from Chicago to Tampa, returning Sat, May 16, priced at $87 found 6 hours ago
Sat, Jul 11 - Sat, Aug 1
ORD
Chicago
TPA
Tampa
$111 Roundtrip, found 6 days ago
$111
Roundtrip
found 6 days ago
Select United flight, departing Sat, Jul 11 from Chicago to Tampa, returning Sat, Aug 1, priced at $111 found 6 days ago
Wed, May 13 - Wed, May 20
RFD
Rockford
MCO
Orlando
$157 Roundtrip, found 12 hours ago
$157
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Wed, May 13 from Rockford to Orlando, returning Wed, May 20, priced at $157 found 12 hours ago

Lake Wales economy flight packages

Price found within the past 48 hours. Click for updated prices.
Kompose Boutique Hotel
3.0-star property

Kompose Boutique Hotel

9.2/10 Wonderful! (4,624 reviews)

Apr 5 - Apr 10

5 night stay

Chicago (CHI) to Tampa (TPA)

Spirit Airlines • Coach

Tampa (TPA) to Chicago (CHI)

Frontier Airlines • Coach
Price was $749, price is now $484 per person
$484
per person
found 1 day ago
Housekeeping everyday should be included The QR check in is annoying A/C makes noice and seems it was working but the room did not change temperature Room smelled muggy

Reviewed on Dec 15, 2025

The Sarasota Modern, a Tribute Portfolio Hotel
4.0-star property

The Sarasota Modern, a Tribute Portfolio Hotel

8.2/10 Very Good! (515 reviews)

Apr 5 - Apr 10

5 night stay

Chicago (CHI) to Tampa (TPA)

Spirit Airlines • Coach

Tampa (TPA) to Chicago (CHI)

Frontier Airlines • Coach
Price was $961, price is now $594 per person
$594
per person
found 1 day ago
The only thing we didn’t like was being charged 30.00 a day to park. Also bathrooms very dark as were the black hallways.

Reviewed on Nov 12, 2022

voco Sarasota by IHG
3.5-star property

voco Sarasota by IHG

9.2/10 Wonderful! (1,001 reviews)

Mar 26 - Mar 29

3 night stay

Chicago (CHI) to Tampa (TPA)

Frontier Airlines • Coach

Tampa (TPA) to Chicago (CHI)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,261, price is now $826 per person
$826
per person
found 3 hours ago
Hotel was great. They are close to restaurants and have a shuttle that will take you places like St Armand’s Circle. They also have beach towels, chairs and umbrellas that you can use at the beach. We would stay at hotel again for sure.

Reviewed on Jun 30, 2024

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Lake Wales packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
The Beachcomber
2.5-star property

The Beachcomber

8/10 Very Good! (1,005 reviews)

Apr 2 - Apr 5

3 night stay

Chicago (ORD) to Tampa (TPA)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,560, price is now $1,273 per person
$1,273
per person
found 20 hours ago
Great location, awesome entertainment, super clean! Be back really soon!

Reviewed on Dec 10, 2025

The Avalon Club
4.0-star property

The Avalon Club

9.4/10 Exceptional! (481 reviews)

Apr 2 - Apr 5

3 night stay

Chicago (ORD) to Tampa (TPA)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $3,039, price is now $2,310 per person
$2,310
per person
found 20 hours ago
You can walk to different restaurants. The only bad thing is that the bed in the master bedroom was not in good condition and the metal base was broken. I had to move to another room within the same unit.

Reviewed on Aug 17, 2025

RumFish Beach at TradeWinds
4.0-star property

RumFish Beach at TradeWinds

8.2/10 Very Good! (1,516 reviews)

Apr 2 - Apr 5

3 night stay

Chicago (ORD) to Tampa (TPA)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,677, price is now $1,362 per person
$1,362
per person
found 20 hours ago
My wife and I travel a lot including international as well. So we have experience and stay in a lot of different hotels and this experience at RumFish is just average and I could have rates alot lower. the staff is friendly and courteous, but the room is just ok, not as nice and updated compared to other hetels I have stay in where is a 5-stars. However, what disappointed me the most is the amenities. I pay in full online on Orbitz, When I book the hotel and its list all the amenities that included, but when I check out, they charge me $185 for the amenities and taxes for 3nights stay. With all my stay over years at hotel, I have never been charge additional for the amenities. It just have included when you pay in full for your booking. So I was very shock and disappointed. I would recommended people to careful when booking at this hotel.

Reviewed on Jan 7, 2026

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More About Flying To Lake Wales from Chicago

Route Information for Flights from Chicago to Lake Wales

Origin Airport IATA Code
CHI
Destination Airport IATA Code
TPA
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Lake Wales

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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.