$44 Cheap flight deals from Tampa (TPA) to Naperville (CHI)

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This Weekend's Flight Deals from Tampa to Naperville

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, Aug 24 - Sun, Aug 31
TPA
Tampa Intl.
MDW
Midway Intl.
$57 Roundtrip, found 2 days ago
$57
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Aug 24 from Tampa Intl. to Midway Intl., returning Sun, Aug 31, priced at $57 found 2 days ago
Sun, Aug 24 - Mon, Aug 25
TPA
Tampa Intl.
ORD
O'Hare Intl.
$201 Roundtrip, found 22 hours ago
$201
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Sun, Aug 24 from Tampa Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $201 found 22 hours ago
Sun, Aug 24 - Mon, Aug 25
SRQ
Sarasota-Bradenton Intl.
ORD
O'Hare Intl.
$471 Roundtrip, found 2 days ago
$471
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sun, Aug 24 from Sarasota-Bradenton Intl. to O'Hare Intl., returning Mon, Aug 25, priced at $471 found 2 days ago

Airfares from $44 One Way, $56 Round Trip from Tampa to Naperville

Prices starting at $56 for return flights and $44 for one-way flights to Naperville were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Oct 24 - Sun, Oct 26
TPA
Tampa
MDW
Chicago
$56 Roundtrip, found 2 days ago
$56
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Oct 24 from Tampa to Chicago, returning Sun, Oct 26, priced at $56 found 2 days ago
Tue, Sep 16 - Sat, Sep 20
TPA
Tampa
ORD
Chicago
$88 Roundtrip, found 1 day ago
$88
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Sep 16 from Tampa to Chicago, returning Sat, Sep 20, priced at $88 found 1 day ago
Sat, Nov 8 - Tue, Nov 11
TPA
Tampa
ORD
Chicago
$157 Roundtrip, found 21 hours ago
$157
Roundtrip
found 21 hours ago
Select Southwest Airlines flight, departing Sat, Nov 8 from Tampa to Chicago, returning Tue, Nov 11, priced at $157 found 21 hours ago
Sat, Nov 8 - Tue, Nov 11
TPA
Tampa
ORD
Chicago
$157 Roundtrip, found 21 hours ago
$157
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Sat, Nov 8 from Tampa to Chicago, returning Tue, Nov 11, priced at $157 found 21 hours ago
Thu, Oct 30 - Mon, Nov 3
TPA
Tampa
ORD
Chicago
$197 Roundtrip, found 4 hours ago
$197
Roundtrip
found 4 hours ago
Select Delta flight, departing Thu, Oct 30 from Tampa to Chicago, returning Mon, Nov 3, priced at $197 found 4 hours ago

Naperville economy flight packages

Price found within the past 48 hours. Click for updated prices.
citizenM Chicago Downtown
4.0-star property

citizenM Chicago Downtown

9.2/10 Wonderful! (3,522 reviews)

Sep 22 - Sep 25

3 night stay

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Coach

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • Coach
Save 100% on your flight
Price was $543, price is now $369 per person
$369
per person
found 1 day ago
I didn’t like when i got there i didn’t get the room i booked online. I was told my room was moved because the one i booked wasn’t up to part & that i was being upgraded but i wasn’t upgraded. My room was very small & i didn’t get a city view like i booked. The room that i was put in faced another building no view of the city at all.

Reviewed on Aug 18, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,679 reviews)

Sep 20 - Sep 23

3 night stay

Orlando (MCO) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,235, price is now $824 per person
$824
per person
found 1 day ago
I recently stayed at the Trump International Hotel & Tower Chicago, and it exceeded every expectation. From the moment I arrived, I was impressed by the warmth and professionalism of the staff. Check-in was smooth and welcoming, and I was personally escorted to my room—which turned out to be nothing short of spectacular. The room itself was spacious, immaculately clean, and beautifully designed with modern touches and classic elegance. Floor-to-ceiling windows offered breathtaking views of the Chicago River and city skyline. The kitchenette was a nice bonus and made the room feel more like a luxury apartment than a typical hotel room. The service throughout my stay was consistently excellent—attentive without being overbearing. Every request was handled promptly and with a smile, and it was clear that the staff genuinely cared about making my stay enjoyable. I also had the chance to dine at Rebar, and the food and views were equally impressive. The atmosphere was relaxed yet refined, and it made for a perfect evening. The location is ideal—walking distance to the Magnificent Mile, Millennium Park, and plenty of restaurants and shops. Despite being in the heart of downtown, the hotel felt like a peaceful retreat above the city. Whether you're visiting Chicago for business or pleasure, I highly recommend the Trump International Hotel. It’s a standout experience in every way—luxury, location, service, and comfort all rolled into one.

Reviewed on Aug 14, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,270 reviews)

Sep 22 - Sep 25

3 night stay

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Coach

Chicago (ORD) to Orlando (MCO)

Spirit Airlines • Coach
Save 100% on your flight
Price was $742, price is now $507 per person
$507
per person
found 1 day ago
Good until next time

Reviewed on Aug 16, 2025

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Naperville packages with premium economy flights

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! (1,991 reviews)

Oct 9 - Oct 12

3 night stay

Tampa (TPA) to Chicago (ORD)

United • PremiumEconomy

Chicago (ORD) to Tampa (TPA)

Delta • PremiumEconomy
Price was $1,642, price is now $1,346 per person
$1,346
per person
found 1 day ago
Excellent hotel. Clean. Love the facility. Convenient to restaurants and shopping areas. Professional staff.

Reviewed on Aug 12, 2025

citizenM Chicago Downtown
4.0-star property

citizenM Chicago Downtown

9.2/10 Wonderful! (3,522 reviews)

Oct 9 - Oct 12

3 night stay

Tampa (TPA) to Chicago (ORD)

United • PremiumEconomy

Chicago (ORD) to Tampa (TPA)

Delta • PremiumEconomy
Price was $1,634, price is now $1,348 per person
$1,348
per person
found 1 day ago
I didn’t like when i got there i didn’t get the room i booked online. I was told my room was moved because the one i booked wasn’t up to part & that i was being upgraded but i wasn’t upgraded. My room was very small & i didn’t get a city view like i booked. The room that i was put in faced another building no view of the city at all.

Reviewed on Aug 18, 2025

Embassy Suites by Hilton Chicago Downtown River North
4.0-star property

Embassy Suites by Hilton Chicago Downtown River North

8.4/10 Very Good! (4,622 reviews)

Oct 9 - Oct 12

3 night stay

Tampa (TPA) to Chicago (ORD)

United • PremiumEconomy

Chicago (ORD) to Tampa (TPA)

Delta • PremiumEconomy
Price was $1,817, price is now $1,506 per person
$1,506
per person
found 1 day ago
Everything was awesome

Reviewed on Aug 10, 2025

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Naperville first class flight packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Chicago NW - Arlington Heights by IHG
2.5-star property

Holiday Inn Express Chicago NW - Arlington Heights by IHG

8.8/10 Excellent! (990 reviews)

Oct 9 - Oct 12

3 night stay

Tampa (TPA) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $942, price is now $895 per person
$895
per person
found 1 day ago
This hotel is located my favorite Japanese grocery market. And rice is served for breakfast.

Reviewed on Feb 18, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
3.5-star property

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

8.6/10 Excellent! (2,367 reviews)

Oct 9 - Oct 12

3 night stay

Tampa (TPA) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $1,201, price is now $1,062 per person
$1,062
per person
found 1 day ago
The staff at as very nice and helpful. The ice machine next door was flooding and had a pile of towels laying there. The carpet in the bedroom was very wet near the window.

Reviewed on Jun 30, 2025

Holiday Inn Express & Suites Bensenville - O'Hare by IHG
3.0-star property

Holiday Inn Express & Suites Bensenville - O'Hare by IHG

8.8/10 Excellent! (1,002 reviews)

Oct 9 - Oct 12

3 night stay

Tampa (TPA) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $1,137, price is now $1,124 per person
$1,124
per person
found 1 day ago
Good condition good stuff

Reviewed on Oct 25, 2024

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More About Flying To Naperville from Tampa

Route Information for Flights from Tampa to Naperville

Origin Airport IATA Code
TPA
Destination Airport IATA Code
CHI
Distance
1013 mi
Direct Flight Airlines
American Airlines, Qatar Airways, Air Canada, JAL, Emirates, Copa Airlines, Swiss, Air New Zealand, United Airlines, Alaska Airlines, Qantas, Royal Jordanian, ANA, Brussels Airlines, Lufthansa, Spirit Airlines, Gulf Air, British Airways
Earliest Flight Arrival
1:06PM UTC
Latest Flight Arrival
10:18PM UTC

Tampa to Naperville

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Easy Flight Cancellation

In most cases, you can cancel flights from Tampa to Naperville online with the same ease as you booked them.

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.