Cheap flights To Wheeling (CHI) from $29

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Cheap Flights to Wheeling from $29 One Way, $56 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Feb 13 - Sun, Feb 22
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$56 Roundtrip, found 2 days ago
$56
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Feb 13 from Sky Harbor Intl. to Midway Intl., returning Sun, Feb 22, priced at $56 found 2 days ago
Sat, Feb 14 - Tue, Feb 17
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$57 Roundtrip, found 23 hours ago
$57
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sat, Feb 14 from Sky Harbor Intl. to O'Hare Intl., returning Tue, Feb 17, priced at $57 found 23 hours ago
Thu, Feb 19 - Tue, Feb 24
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$57 Roundtrip, found 14 hours ago
$57
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Thu, Feb 19 from Sky Harbor Intl. to O'Hare Intl., returning Tue, Feb 24, priced at $57 found 14 hours ago
Mon, Mar 23 - Wed, Apr 1
DEN
Denver Intl.
ORD
O'Hare Intl.
$82 Roundtrip, found 10 hours ago
$82
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Mon, Mar 23 from Denver Intl. to O'Hare Intl., returning Wed, Apr 1, priced at $82 found 10 hours ago
Wed, Feb 4 - Tue, Feb 10
BOS
Logan Intl.
ORD
O'Hare Intl.
$116 Roundtrip, found 6 days ago
$116
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Feb 4 from Logan Intl. to O'Hare Intl., returning Tue, Feb 10, priced at $116 found 6 days ago
Sat, Jan 31 - Sat, Feb 7
BOS
Logan Intl.
MDW
Midway Intl.
$116 Roundtrip, found 1 day ago
$116
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Jan 31 from Logan Intl. to Midway Intl., returning Sat, Feb 7, priced at $116 found 1 day ago
Wed, Feb 18 - Wed, Feb 25
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$124 Roundtrip, found 6 days ago
$124
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Feb 18 from Los Angeles Intl. to O'Hare Intl., returning Wed, Feb 25, priced at $124 found 6 days ago
Tue, Feb 24 - Tue, Feb 24
BOS
Logan Intl.
ORD
O'Hare Intl.
$135 Roundtrip, found 2 days ago
$135
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Feb 24 from Logan Intl. to O'Hare Intl., returning Tue, Feb 24, priced at $135 found 2 days ago
Mon, Mar 23 - Wed, Mar 25
BOS
Logan Intl.
ORD
O'Hare Intl.
$135 Roundtrip, found 2 days ago
$135
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Mar 23 from Logan Intl. to O'Hare Intl., returning Wed, Mar 25, priced at $135 found 2 days ago
Wed, May 27 - Sat, May 30
BOS
Logan Intl.
ORD
O'Hare Intl.
$135 Roundtrip, found 12 hours ago
$135
Roundtrip
found 12 hours ago
Select Delta flight, departing Wed, May 27 from Logan Intl. to O'Hare Intl., returning Sat, May 30, priced at $135 found 12 hours ago

Wheeling Flight Information

Traveling To
Wheeling
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Southwest Airlines, American Airlines, United, Delta, Spirit Airlines, JetBlue Airways
Flight Price
$56
Earliest Departing Flight
Latest Departing Flight

Flights Review

Mar 10, 2018

Great overall service. Smooth landing. Plane was even early.

A verified traveler
Denver to Chicago · United

Book Your Flight & Hotel Together & Save

Wheeling economy flight packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
4.0-star property

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

Mar 9 - Mar 14

5 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Boston (BOS)

Southwest Airlines • Coach
Save 100% on your flight
Price was $643, price is now $476 per person
$476
per person
found 1 day ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Mar 9 - Mar 13

4 night stay

Boston (BOS) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,289, price is now $875 per person
$875
per person
found 1 day ago
SpringHill Suites by Marriott Chicago Southwest at Burr Ridge/Hinsdale
3.0-star property

SpringHill Suites by Marriott Chicago Southwest at Burr Ridge/Hinsdale

Mar 8 - Mar 14

6 night stay

Boston (BOS) to Chicago (ORD)

Delta • Coach

Chicago (ORD) to Boston (BOS)

Southwest Airlines • Coach
Save 100% on your flight
Price was $674, price is now $486 per person
$486
per person
found 1 day ago
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Wheeling 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! (2,790 reviews)

Feb 27 - Mar 4

5 night stay

Dallas (DFW) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,085, price is now $740 per person
$740
per person
found 9 hours ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Feb 27 - Mar 4

5 night stay

Dallas (DFW) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $1,888, price is now $1,205 per person
$1,205
per person
found 9 hours ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

Waldorf Astoria Chicago
5.0-star property

Waldorf Astoria Chicago

9.4/10 Exceptional! (1,000 reviews)

Feb 27 - Mar 4

5 night stay

Dallas (DFW) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $1,881, price is now $1,325 per person
$1,325
per person
found 9 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

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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.