S$128 Cheap Flights from Orlando to Chicago

View S$128 flight on Wed, 11 Feb, 2026Opens in a new window

Popular airlines from Orlando Intl. Airport (MCO) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Orlando to Chicago (MCO-ORD)

Prices were available within the past 7 days and start at S$128 for one-way flights and S$254 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 29 Jan - Mon, 2 Feb
MCO
Orlando
ORD
Chicago
S$254 Return, found 1 day ago
S$254
Return
found 1 day ago
Select Delta flight, departing Thu, 29 Jan from Orlando to Chicago, returning Mon, 2 Feb, priced at S$254 found 1 day ago
Delta
Thu, 29 Jan - Mon, 2 Feb
MCO
Orlando
ORD
Chicago
S$267 Return, found 1 day ago
S$267
Return
found 1 day ago
Select Delta flight, departing Thu, 29 Jan from Orlando to Chicago, returning Mon, 2 Feb, priced at S$267 found 1 day ago
American Airlines
Thu, 29 Jan - Mon, 2 Feb
MCO
Orlando
ORD
Chicago
S$278 Return, found 1 day ago
S$278
Return
found 1 day ago
Select American Airlines flight, departing Thu, 29 Jan from Orlando to Chicago, returning Mon, 2 Feb, priced at S$278 found 1 day ago
United
Thu, 29 Jan - Mon, 2 Feb
MCO
Orlando
ORD
Chicago
S$278 Return, found 1 day ago
S$278
Return
found 1 day ago
Select United flight, departing Thu, 29 Jan from Orlando to Chicago, returning Mon, 2 Feb, priced at S$278 found 1 day ago
United
Thu, 29 Jan - Mon, 2 Feb
MCO
Orlando
ORD
Chicago
S$279 Return, found 1 day ago
S$279
Return
found 1 day ago
Select United flight, departing Thu, 29 Jan from Orlando to Chicago, returning Mon, 2 Feb, priced at S$279 found 1 day ago
American Airlines
Thu, 29 Jan - Mon, 2 Feb
MCO
Orlando
ORD
Chicago
S$297 Return, found 1 day ago
S$297
Return
found 1 day ago
Select American Airlines flight, departing Thu, 29 Jan from Orlando to Chicago, returning Mon, 2 Feb, priced at S$297 found 1 day ago
American Airlines
Thu, 29 Jan - Mon, 2 Feb
MCO
Orlando
ORD
Chicago
S$308 Return, found 1 day ago
S$308
Return
found 1 day ago
Select American Airlines flight, departing Thu, 29 Jan from Orlando to Chicago, returning Mon, 2 Feb, priced at S$308 found 1 day ago
American Airlines
Thu, 29 Jan - Mon, 2 Feb
MCO
Orlando
ORD
Chicago
S$309 Return, found 1 day ago
S$309
Return
found 1 day ago
Select American Airlines flight, departing Thu, 29 Jan from Orlando to Chicago, returning Mon, 2 Feb, priced at S$309 found 1 day ago
American Airlines
Thu, 29 Jan - Mon, 2 Feb
MCO
Orlando
ORD
Chicago
S$322 Return, found 1 day ago
S$322
Return
found 1 day ago
Select American Airlines flight, departing Thu, 29 Jan from Orlando to Chicago, returning Mon, 2 Feb, priced at S$322 found 1 day ago
Delta
Thu, 29 Jan - Mon, 2 Feb
MCO
Orlando
ORD
Chicago
S$326 Return, found 1 day ago
S$326
Return
found 1 day ago
Select Delta flight, departing Thu, 29 Jan from Orlando to Chicago, returning Mon, 2 Feb, priced at S$326 found 1 day ago

Find the cheapest month to fly from Orlando (MCO) to Chicago (ORD)

February is typically the cheapest month to fly

From S$75 - S$212 per traveller.

Frequently asked questions

How much is a flight from Orlando Intl. Airport to O'Hare Airport?
Round-trip flights from Orlando Intl. Airport (MCO) to O'Hare Intl. Airport (ORD) start from S$254. This figure is based on fares available within the last 7 days on Expedia for flights departing within the next year — book today to avoid missing out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from MCO to O'Hare Intl. Airport (ORD)?
Most flights can be cancelled online, but every airline has its own set of terms and conditions. If you do decide to cancel your flight, visit our Customer Service Portal and follow the instructions.
How do I find cheap flights from Orlando Intl. Airport to O'Hare Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Orlando Intl. Airport to O'Hare Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Orlando Intl. Airport (MCO) to O'Hare Intl. Airport (ORD)?
The flight distance between MCO (MCO) and ORD (ORD) is 1,600 kilometres. Work your way through your travel song playlist or finish that novel and the journey will zip by.
Which airlines fly direct from MCO to ORD?
Whether you need a return or one-way flight, you'll have your choice of airlines that will take you straight from Orlando Intl. Airport (MCO) to ORD. These are some of the most popular ones:

  • United Airlines - (UA) with 173 monthly flights
  • American Airlines - (AA) with 121 monthly flights
  • Spirit Airlines - (NK) with 60 monthly flights
  • Southwest Airlines - (WN) with 30 monthly flights

Are MCO to ORD flight tickets cheaper when they're purchased at the last minute?
Last-minute planners can sometimes score a bargain, with some super cheap airfares from Orlando Intl. Airport to O'Hare Airport appearing a few weeks before the departure date. If you'd rather plan ahead, Expedia compares and updates the best flight deals continuously — as early as a year in advance in some cases. It does depend on the carrier though, as not every airline releases prices so far in advance.

Travel information

Origin airport
Orlando Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Return price
S$253
Distance
1610 km
Average flight time
2 hours 7 mins

Book with confidence

Flights from Orlando to Chicago

There are several airlines that operate frequent flights from Orlando (MCO) to Chicago (ORD) including

The earliest flight leaves Orlando Intl. Airport at 05:50 and arrives at O'Hare Intl. Airport at 07:44. The last flight of the day departs Orlando at 20:53 and arrives at Chicago at 22:50.

The flight distance from Orlando to Chicago is about 1627 km, the shortest flight is 02 hours 49 minutes with United Airlines.

Expedia lets you search across the largest number of airlines and Chicago flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Orlando Chicago flight!

Browse through dozens of options and rest assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Orlando to Chicago trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Chicago flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from Orlando to Chicago with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!

Flights from Orlando to Chicago

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