$71 Cheap flight deals from Tampa (TPA) to Highland Park (CHI)
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This Weekend's Flight Deals from Tampa to Highland Park
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.
TPA
Tampa Intl.
MDW
Midway Intl.
$342 Roundtrip, found 8 hours ago
$342
Roundtrip
found 8 hours ago
TPA
Tampa Intl.
ORD
O'Hare Intl.
$349 Roundtrip, found 12 hours ago
$349
Roundtrip
found 12 hours ago
SRQ
Sarasota-Bradenton Intl.
ORD
O'Hare Intl.
$520 Roundtrip, found 2 days ago
$520
Roundtrip
found 2 days ago
SRQ
Sarasota-Bradenton Intl.
MDW
Midway Intl.
$535 Roundtrip, found 2 days ago
$535
Roundtrip
found 2 days ago
Airfares from $71 One Way, $164 Round Trip from Tampa to Highland Park
Prices starting at $164 for return flights and $71 for one-way flights to Highland Park were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
TPA
Tampa
ORD
Chicago
$164 Roundtrip, found 1 day ago
$164
Roundtrip
found 1 day ago
TPA
Tampa
RFD
Rockford
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
TPA
Tampa
ORD
Chicago
$199 Roundtrip, found 2 days ago
$199
Roundtrip
found 2 days ago
TPA
Tampa
MDW
Chicago
$199 Roundtrip, found 4 days ago
$199
Roundtrip
found 4 days ago
TPA
Tampa
MDW
Chicago
$213 Roundtrip, found 4 days ago
$213
Roundtrip
found 4 days ago
Highland Park economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Omni Chicago Hotel
9.2/10 Wonderful! (1,821 reviews)
Aug 27 - Aug 31
4 night stay
Orlando (MCO) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Orlando (MCO)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,199, price is now $809 per person
$809
per person
found 2 days ago
The room was very clean and spacious. Very helpful staff. We were able to get into our room early and get a later checkout due to our flights. The Doorman were also very courteous and helpful. Great location!
Reviewed on Jul 3, 2026
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (4,518 reviews)
Aug 27 - Aug 31
4 night stay
Orlando (MCO) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Orlando (MCO)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,377, price is now $889 per person
$889
per person
found 2 days ago
Great location and the rooftop bar was a bonus.
Reviewed on Jul 3, 2026
4.0-star property
Level Chicago Fulton Market
9.2/10 Wonderful! (512 reviews)
Aug 27 - Aug 31
4 night stay
Orlando (MCO) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Orlando (MCO)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,370, price is now $905 per person
$905
per person
found 1 day ago
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026
More About Flying To Highland Park from Tampa
Route Information for Flights from Tampa to Highland Park
Origin Airport IATA Code | TPA |
|---|---|
Destination Airport IATA Code | CHI |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
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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.