$49 Cheap flight deals from Tampa (TPA) to Wheeling (CHI)

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This Weekend's Flight Deals from Tampa to Wheeling

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, Sep 6 - Thu, Sep 10
SRQ
Sarasota-Bradenton Intl.
RFD
Greater Rockford
$164 Roundtrip, found 1 hour ago
$164
Roundtrip
found 1 hour ago
Select Allegiant Air flight, departing Sun, Sep 6 from Sarasota-Bradenton Intl. to Greater Rockford, returning Thu, Sep 10, priced at $164 found 1 hour ago
Fri, Sep 4 - Mon, Sep 7
PIE
St. Petersburg-Clearwater Intl.
RFD
Greater Rockford
$275 Roundtrip, found 6 days ago
$275
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Fri, Sep 4 from St. Petersburg-Clearwater Intl. to Greater Rockford, returning Mon, Sep 7, priced at $275 found 6 days ago
Fri, Sep 4 - Mon, Sep 7
PIE
St. Petersburg-Clearwater Intl.
RFD
Greater Rockford
$275 Roundtrip, found 6 days ago
$275
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Fri, Sep 4 from St. Petersburg-Clearwater Intl. to Greater Rockford, returning Mon, Sep 7, priced at $275 found 6 days ago
Sat, Sep 5 - Tue, Sep 8
TPA
Tampa Intl.
MDW
Midway Intl.
$278 Roundtrip, just found
$278
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Sep 5 from Tampa Intl. to Midway Intl., returning Tue, Sep 8, priced at $278 just found

Airfares from $49 One Way, $122 Round Trip from Tampa to Wheeling

Prices starting at $122 for return flights and $49 for one-way flights to Wheeling were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Jan 14 - Sun, Jan 24
SRQ
Sarasota
RFD
Rockford
$122 Roundtrip, found 2 days ago
$122
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Jan 14 from Sarasota to Rockford, returning Sun, Jan 24, priced at $122 found 2 days ago
Fri, Oct 23 - Mon, Oct 26
PIE
St. Petersburg
RFD
Rockford
$143 Roundtrip, found 5 days ago
$143
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Fri, Oct 23 from St. Petersburg to Rockford, returning Mon, Oct 26, priced at $143 found 5 days ago
Fri, Dec 4 - Mon, Dec 7
TPA
Tampa
ORD
Chicago
$158 Roundtrip, just found
$158
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Dec 4 from Tampa to Chicago, returning Mon, Dec 7, priced at $158 just found
Sat, Oct 10 - Mon, Oct 12
TPA
Tampa
MDW
Chicago
$200 Roundtrip, found 4 days ago
$200
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Oct 10 from Tampa to Chicago, returning Mon, Oct 12, priced at $200 found 4 days ago
Thu, Oct 1 - Sat, Oct 3
TPA
Tampa
RFD
Rockford
$208 Roundtrip, found 3 days ago
$208
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Oct 1 from Tampa to Rockford, returning Sat, Oct 3, priced at $208 found 3 days ago

Wheeling economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (2,960 reviews)

Oct 15 - Oct 19

4 night stay

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,247, price is now $911 per person
$911
per person
found 1 day ago

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (5,045 reviews)

Oct 9 - Oct 11

2 night stay

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,739, price is now $1,162 per person
$1,162
per person
found 1 day ago
The staff was very helpful, we loved the amenities, the breakfast was good, a lot of options every day

Reviewed on Aug 31, 2026

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (3,577 reviews)

Oct 15 - Oct 19

4 night stay

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,637, price is now $1,117 per person
$1,117
per person
found 1 day ago
The staff was very friendly and the room was always clean and organized. I was a bit nervous what to expect as a solo traveler and it being my first time staying in Chicago but this was the perfect hotel for the trip. It always felt safe on property and very close to all the main things I wanted to see.

Reviewed on Aug 31, 2026

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More About Flying To Wheeling from Tampa

Route Information for Flights from Tampa to Wheeling

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

Tampa to Wheeling

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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.