$97 Cheap flight deals from Tampa (TPA) to DeKalb (CHI)

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This Weekend's Flight Deals from Tampa to DeKalb

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.

Sat, Jul 11 - Wed, Jul 15
TPA
Tampa Intl.
ORD
O'Hare Intl.
$483 Roundtrip, found 19 hours ago
$483
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Sat, Jul 11 from Tampa Intl. to O'Hare Intl., returning Wed, Jul 15, priced at $483 found 19 hours ago
Sat, Jul 11 - Mon, Jul 20
SRQ
Sarasota-Bradenton Intl.
ORD
O'Hare Intl.
$528 Roundtrip, found 20 hours ago
$528
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Sat, Jul 11 from Sarasota-Bradenton Intl. to O'Hare Intl., returning Mon, Jul 20, priced at $528 found 20 hours ago

Airfares from $97 One Way, $193 Round Trip from Tampa to DeKalb

Prices starting at $193 for return flights and $97 for one-way flights to DeKalb were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Sep 5 - Tue, Sep 8
TPA
Tampa
RFD
Rockford
$193 Roundtrip, found 4 days ago
$193
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Sep 5 from Tampa to Rockford, returning Tue, Sep 8, priced at $193 found 4 days ago
Tue, Sep 1 - Thu, Sep 3
TPA
Tampa
RFD
Rockford
$199 Roundtrip, found 6 days ago
$199
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Sep 1 from Tampa to Rockford, returning Thu, Sep 3, priced at $199 found 6 days ago
Thu, Oct 29 - Mon, Nov 2
TPA
Tampa
ORD
Chicago
$205 Roundtrip, found 6 days ago
$205
Roundtrip
found 6 days ago
Select United flight, departing Thu, Oct 29 from Tampa to Chicago, returning Mon, Nov 2, priced at $205 found 6 days ago
Wed, Oct 14 - Tue, Oct 20
TPA
Tampa
ORD
Chicago
$210 Roundtrip, found 4 hours ago
$210
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Tampa to Chicago, returning Tue, Oct 20, priced at $210 found 4 hours ago
Sat, Jul 25 - Tue, Jul 28
SRQ
Sarasota
ORD
Chicago
$232 Roundtrip, found 4 days ago
$232
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Jul 25 from Sarasota to Chicago, returning Tue, Jul 28, priced at $232 found 4 days ago

DeKalb 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! (2,809 reviews)

Aug 15 - Aug 19

4 night stay

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $693, price is now $472 per person
$472
per person
found 1 day ago
The hotel did not clean our room until we contacted the staff of when contacted took remain uncleared . It also seemed like some of the valet employees were either new or there was a lack of communication, because our vehicle was delayed several times—even beyond the estimated pickup time. Overall, there is definitely room for improvement in both housekeeping and valet service.

Reviewed on Jul 6, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,566 reviews)

Aug 15 - Aug 19

4 night stay

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,177, price is now $798 per person
$798
per person
found 1 day ago
All stupendous!

Reviewed on Jul 6, 2026

Level Chicago Fulton Market
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)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,368, price is now $929 per person
$929
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

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More About Flying To DeKalb from Tampa

Route Information for Flights from Tampa to DeKalb

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

Tampa to DeKalb

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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.