$59 Cheap flight deals from Tampa (TPA) to Oak Brook (CHI)

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This Weekend's Flight Deals from Tampa to Oak Brook

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, Jun 7 - Wed, Jun 10
TPA
Tampa Intl.
MDW
Midway Intl.
$306 Roundtrip, found 5 days ago
$306
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Jun 7 from Tampa Intl. to Midway Intl., returning Wed, Jun 10, priced at $306 found 5 days ago
Sun, Jun 7 - Mon, Jun 8
TPA
Tampa Intl.
ORD
O'Hare Intl.
$378 Roundtrip, found 8 hours ago
$378
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sun, Jun 7 from Tampa Intl. to O'Hare Intl., returning Mon, Jun 8, priced at $378 found 8 hours ago
Sat, Jun 6 - Mon, Jun 8
SRQ
Sarasota-Bradenton Intl.
ORD
O'Hare Intl.
$450 Roundtrip, found 13 hours ago
$450
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, Jun 6 from Sarasota-Bradenton Intl. to O'Hare Intl., returning Mon, Jun 8, priced at $450 found 13 hours ago
Sat, Jun 6 - Mon, Jun 8
SRQ
Sarasota-Bradenton Intl.
RFD
Greater Rockford
$450 Roundtrip, found 13 hours ago
$450
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, Jun 6 from Sarasota-Bradenton Intl. to Greater Rockford, returning Mon, Jun 8, priced at $450 found 13 hours ago

Airfares from $59 One Way, $124 Round Trip from Tampa to Oak Brook

Prices starting at $124 for return flights and $59 for one-way flights to Oak Brook 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, Oct 29 - Mon, Nov 2
TPA
Tampa
ORD
Chicago
$124 Roundtrip, found 5 hours ago
$124
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Thu, Oct 29 from Tampa to Chicago, returning Mon, Nov 2, priced at $124 found 5 hours ago
Wed, Jul 1 - Wed, Jul 8
TPA
Tampa
RFD
Rockford
$181 Roundtrip, found 3 days ago
$181
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Jul 1 from Tampa to Rockford, returning Wed, Jul 8, priced at $181 found 3 days ago
Sat, Aug 15 - Tue, Sep 15
TPA
Tampa
ORD
Chicago
$187 Roundtrip, found 2 days ago
$187
Roundtrip
found 2 days ago
Select United flight, departing Sat, Aug 15 from Tampa to Chicago, returning Tue, Sep 15, priced at $187 found 2 days ago
Wed, Sep 2 - Tue, Sep 8
TPA
Tampa
MDW
Chicago
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Sep 2 from Tampa to Chicago, returning Tue, Sep 8, priced at $197 found 2 days ago
Thu, Oct 1 - Mon, Oct 5
TPA
Tampa
MDW
Chicago
$203 Roundtrip, found 2 days ago
$203
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Oct 1 from Tampa to Chicago, returning Mon, Oct 5, priced at $203 found 2 days ago

Oak Brook economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
4.0-star property

Hotel Saint Clair- Magnificent Mile

8.4/10 Very Good! (1,941 reviews)

Jul 18 - Jul 21

3 night stay

Orlando (MCO) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Orlando (MCO)

Frontier Airlines • Coach
Price was $748, price is now $554 per person
$554
per person
found 4 hours ago
The hotel needs to invest in a service elevator for their employees because there can only be five people on the elevator at a time and there’s 16 floors and it takes forever before you can catch an elevator. Also, the room set up. The beds are super close to the wall in entryway so it makes it awkward to navigate. They need to make an adjustment. The sinks are super small with no room to really lay out your toiletries if needed.. The thermostat in my room in particular did not work even though a worker came in and tried to reset it and it was 40° in the room was reading 69° with no heat. Nobody came during the entire weekend to change the bedsheets to give us change switch out the trash. There was also no ironing board or iron in our rooms. Photographed shows robes in the rooms. There are no robes in the room. Everything we needed every time we had to calm down for them to bring it up.

Reviewed on May 4, 2026

Hilton Chicago O'Hare Airport
4.0-star property

Hilton Chicago O'Hare Airport

8.4/10 Very Good! (2,310 reviews)

Jul 22 - Jul 26

4 night stay

Orlando (MCO) to Chicago (ORD)

American Airlines • Non-stop • Coach

Chicago (ORD) to Orlando (MCO)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,011, price is now $715 per person
$715
per person
found 1 day ago
This place gets 3 stars from me only due to its great location. It's in rather poor repair and its overall appearance and upkeep do not reflect well on the Hilton brand. It seems clear that property ownership are not bothering to put money into it because they know they will get traffic from the airport.

Reviewed on Feb 25, 2026

DoubleTree by Hilton Chicago - Alsip
4.0-star property

DoubleTree by Hilton Chicago - Alsip

8.4/10 Very Good! (1,056 reviews)

Jul 17 - Jul 20

3 night stay

Tampa (TPA) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Price was $881, price is now $666 per person
$666
per person
found 1 day ago
Staff was friendly and organized, room was clean, quiet and comfortable,

Reviewed on Nov 17, 2025

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Oak Brook first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (4,258 reviews)

Jul 9 - Jul 12

3 night stay

Tampa (TPA) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $1,783, price is now $1,381 per person
$1,381
per person
found 3 hours ago
Great option! Great location! Great breakfast and friendly staff!

Reviewed on May 30, 2026

Waldorf Astoria Chicago
5.0-star property

Waldorf Astoria Chicago

9.4/10 Exceptional! (1,001 reviews)

Jul 9 - Jul 12

3 night stay

Tampa (TPA) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Tampa (TPA)

Frontier Airlines • FirstClass
Save 100% on your flight
Price was $2,384, price is now $1,736 per person
$1,736
per person
found 3 hours ago
Lovely room and spacious bathroom plus all of the high end touches (robes, slippers to soft mats and towels and great bath products and loved the nespresso maker!) View was not great but gym and lobby made up for it; bar was too crowded and we couldn’t get a late checkout but at least it was noon and they held our bags for a few hours!

Reviewed on Dec 31, 2025

The Peninsula Chicago
5.0-star property

The Peninsula Chicago

9.8/10 Exceptional! (1,005 reviews)

Jul 9 - Jul 12

3 night stay

Tampa (TPA) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $2,549, price is now $1,921 per person
$1,921
per person
found 3 hours ago
Everything was superb. The only “complaint “ I have, is that I paid for a city view room, but actually looked at the side of one building. Other than that, we lived the stay.

Reviewed on Oct 24, 2025

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More About Flying To Oak Brook from Tampa

Route Information for Flights from Tampa to Oak Brook

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

Tampa to Oak Brook

Looking for cheap Tampa to Oak Brook flights? Orbitz has the cheapest air fares for flights from Tampa to Oak Brook. Plus, with our cutting-edge mobile tools, travel planning has never been easier or more wallet-friendly.

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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.