$40 Cheap flight deals from Orlando (ORL) to Chicago (CHI)

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This Weekend's Flight Deals from Orlando to Chicago

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, Oct 4 - Mon, Oct 20
MCO
Orlando Intl.
MDW
Midway Intl.
$105 Roundtrip, found 4 days ago
$105
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Oct 4 from Orlando Intl. to Midway Intl., returning Mon, Oct 20, priced at $105 found 4 days ago
Sat, Oct 4 - Tue, Oct 7
MCO
Orlando Intl.
ORD
O'Hare Intl.
$184 Roundtrip, found 1 hour ago
$184
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Oct 4 from Orlando Intl. to O'Hare Intl., returning Tue, Oct 7, priced at $184 found 1 hour ago

Airfares from $40 One Way, $80 Round Trip from Orlando to Chicago

Prices starting at $80 for return flights and $40 for one-way flights to Chicago 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
MCO
Orlando
ORD
Chicago
$80 Roundtrip, just found
$80
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Oct 24 from Orlando to Chicago, returning Sun, Oct 26, priced at $80 just found
Thu, Dec 4 - Mon, Dec 8
MCO
Orlando
ORD
Chicago
$80 Roundtrip, just found
$80
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Dec 4 from Orlando to Chicago, returning Mon, Dec 8, priced at $80 just found
Thu, Dec 25 - Wed, Dec 31
MCO
Orlando
ORD
Chicago
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select United flight, departing Thu, Dec 25 from Orlando to Chicago, returning Wed, Dec 31, priced at $157 found 1 day ago
Thu, Dec 25 - Wed, Dec 31
MCO
Orlando
ORD
Chicago
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Dec 25 from Orlando to Chicago, returning Wed, Dec 31, priced at $157 found 1 day ago
Thu, Dec 25 - Wed, Dec 31
MCO
Orlando
ORD
Chicago
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Dec 25 from Orlando to Chicago, returning Wed, Dec 31, priced at $157 found 1 day ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (1,920 reviews)

Oct 31 - Nov 2

2 night stay

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $435, price is now $280 per person
$280
per person
found 1 day ago
This property really wants to be a luxury hotel, but they repeatedly missed the mark. Everyone who worked there was really nice and apologetic, but they made promises they did not keep. One gets charged an "urban experience fee" of $25/ day for staying at this hotel. This fee gives you $15 towards food at the restaurants (which are okay, but the service is incredibly slow because there is only one kitchen across the restaurants), and the fee also covers guest passes to a health club that wasn't open during the times I was free, so I was basically forced to pay $25/ day for $15 credit towards their restaurants. My room had a nice view.

Reviewed on Sep 21, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,427 reviews)

Oct 31 - Nov 2

2 night stay

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Price was $849, price is now $441 per person
$441
per person
found 1 day ago
One day didn’t receive room service

Reviewed on Sep 2, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
4.0-star property

The Allegro Royal Sonesta Hotel Chicago Loop

9/10 Wonderful! (2,027 reviews)

Oct 31 - Nov 2

2 night stay

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $429, price is now $287 per person
$287
per person
found 1 day ago
Attitude of the people was outstanding!! Very friendly and helpful.

Reviewed on Jun 13, 2025

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More About Flying To Chicago from Orlando

Route Information for Flights from Orlando to Chicago

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

Flights from Orlando to Chicago

Orlando International Airport

Locating cheap flights from Orlando can be simple with Orbitz.com. The site allows travelers to search a variety of airlines at one time in order to locate the best deals on tickets. Orlando International Airport is located just nine miles southeast of downtown Orlando on Airport Boulevard. Forty-three airlines serve the Orlando International Airport, including AirTran, Continental, United and World Atlantic. Orbitz.com provides air tickets for the majority of these airlines, which is perfect for travelers on a budget.

Parking at Orlando International Airport

Orlando International Airport offers a variety of parking options. The short-term cell phone lot is free for dropping off and picking up passengers. Garage and lot parking is available for both short-term and long-term use and is charged by the day. Valet parking is available for an additional charge and they offer car detailing at a flat rate.

Transportation to the Airport

Orbitz.com can provide information on rental cars in the area. Rental fees may vary depending on the vehicle that you rent. Metered taxi services are available, and many hotels offer free shuttle services to and from the airport. Limos are available to rent by the hour, and the local bus is available for a flat fee depending on your location of origin.

Restaurants at Orlando International

Orlando International Airport offers a variety of options for travelers that want to grab a snack or a meal before boarding the flight. Restaurants include Krispy Kreme and Starbucks, which features a variety of gourmet coffees and pastries. Orbitz.com is perfect for travelers looking for cheap flights from Orlando.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Frequently asked questions

Are there non-stop flights from Orlando to Chicago?
Get set to hit the "book" button because there are 5 airlines that operate nonstop services from MCO to O'Hare Airport. Take to the air in comfort on board one of these quality carriers:

  • United Airlines
  • American Airlines
  • Spirit Airlines
  • Southwest Airlines
  • Frontier Airlines

What is the shortest flight from Orlando to Chicago?
It can take as little as 2 hours and 45 minutes. If you strongly believe your vacation hours should be spent 'vacationing' instead of flying, you'll enjoy the ride from Orlando to Chicago.
What airlines fly from Orlando to Chicago most frequently?
Below are the airlines that frequently fly between MCO to O'Hare Intl. Airport (ORD). No matter what you're looking for in a carrier, you're sure to find one that suits your travel plans among these: United Airlines - (UA) with 143 flights every month American Airlines - (AA) with 112 flights every month Spirit Airlines - (NK) with 60 flights every month Southwest Airlines - (WN) with 39 flights every month
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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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.