$30 Cheap flight deals from Orlando (ORL) to Wheeling (CHI)

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This Weekend's Flight Deals from Orlando to Wheeling

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, Jan 11 - Tue, Jan 13
MCO
Orlando Intl.
MDW
Midway Intl.
$215 Roundtrip, found 7 hours ago
$215
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sun, Jan 11 from Orlando Intl. to Midway Intl., returning Tue, Jan 13, priced at $215 found 7 hours ago
Sat, Jan 10 - Sun, Jan 11
MCO
Orlando Intl.
ORD
O'Hare Intl.
$244 Roundtrip, just found
$244
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jan 10 from Orlando Intl. to O'Hare Intl., returning Sun, Jan 11, priced at $244 just found
Sat, Jan 10 - Sun, Jan 11
MCO
Orlando Intl.
RFD
Greater Rockford
$421 Roundtrip, found 1 day ago
$421
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jan 10 from Orlando Intl. to Greater Rockford, returning Sun, Jan 11, priced at $421 found 1 day ago

Airfares from $30 One Way, $59 Round Trip from Orlando to Wheeling

Prices starting at $59 for return flights and $30 for one-way flights to Wheeling 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, Feb 5 - Sun, Feb 8
MCO
Orlando
MDW
Chicago
$59 Roundtrip, found 8 hours ago
$59
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, Feb 5 from Orlando to Chicago, returning Sun, Feb 8, priced at $59 found 8 hours ago
Sat, Jan 24 - Mon, Feb 2
MCO
Orlando
ORD
Chicago
$59 Roundtrip, found 19 hours ago
$59
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, Jan 24 from Orlando to Chicago, returning Mon, Feb 2, priced at $59 found 19 hours ago
Fri, Jan 30 - Fri, Feb 6
MCO
Orlando
MDW
Chicago
$62 Roundtrip, found 4 days ago
$62
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Jan 30 from Orlando to Chicago, returning Fri, Feb 6, priced at $62 found 4 days ago
Wed, Jan 21 - Mon, Jan 26
MCO
Orlando
ORD
Chicago
$78 Roundtrip, found 4 days ago
$78
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Jan 21 from Orlando to Chicago, returning Mon, Jan 26, priced at $78 found 4 days ago
Wed, Feb 11 - Wed, Feb 18
MCO
Orlando
ORD
Chicago
$155 Roundtrip, found 12 hours ago
$155
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Wed, Feb 11 from Orlando to Chicago, returning Wed, Feb 18, priced at $155 found 12 hours ago

Wheeling 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! (2,365 reviews)

Feb 13 - Feb 16

3 night stay

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $332, price is now $221 per person
$221
per person
found 9 hours ago
Always easy and clean and safe

Reviewed on Nov 18, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Feb 13 - Feb 16

3 night stay

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $452, price is now $285 per person
$285
per person
found 9 hours ago
Staff is TOP NOTCH! I am in a wheelchair right now, recovering from a knee surgery, and staff could not have been more solicitous and helpful. Also, when we checked in, upon learning of my daughter‘s birthday on Christmas, the front desk representative gave us a complementary room upgrade and sent up chocolates! The room was very clean and the shower was fantastic. Not enough good words about the buffet, as long as you’re clear that it is a “breakfast“ buffet and not a “brunch“ buffet :-). I think I was expecting a sliced roast beef and an omelette bar, but it is in fact a very extensive selection of breakfast foods. The restaurant recommendation was spot on. We had a delicious dinner of fine Mediterranean/Sardinian foodat Nora’s next door and enjoyed it immensely. I have now joined the capital RIU club and plan on spending much more time at their other properties, particularly in Costa Rica, where I am moving next month. Kudos to all, and thank you for our wonderful stay!

Reviewed on Dec 28, 2025

Springhill Suites by Marriott Chicago Downtown/ River North
3.5-star property

Springhill Suites by Marriott Chicago Downtown/ River North

9.2/10 Wonderful! (1,006 reviews)

Feb 13 - Feb 16

3 night stay

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $371, price is now $242 per person
$242
per person
found 4 hours ago
Great location and friendly staff.

Reviewed on May 14, 2025

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More About Flying To Wheeling from Orlando

Route Information for Flights from Orlando to Wheeling

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

Orlando to Wheeling

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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.