S$127 Cheap Flights from Orlando to Chicago

View S$127 flight on Tue, 4 Nov, 2025Opens 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$127 for one-way flights and S$294 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sat, 20 Sep - Sun, 21 Sep
MCO
Orlando
ORD
Chicago
S$294 Return, found 5 days ago
S$294
Return
found 5 days ago
Select United flight, departing Sat, 20 Sep from Orlando to Chicago, returning Sun, 21 Sep, priced at S$294 found 5 days ago
United
Sat, 13 Sep - Tue, 16 Sep
MCO
Orlando
ORD
Chicago
S$302 Return, found 3 days ago
S$302
Return
found 3 days ago
Select United flight, departing Sat, 13 Sep from Orlando to Chicago, returning Tue, 16 Sep, priced at S$302 found 3 days ago
United
Sun, 14 Sep - Tue, 16 Sep
MCO
Orlando
ORD
Chicago
S$321 Return, found 2 days ago
S$321
Return
found 2 days ago
Select United flight, departing Sun, 14 Sep from Orlando to Chicago, returning Tue, 16 Sep, priced at S$321 found 2 days ago
Delta
Sun, 14 Sep - Tue, 16 Sep
MCO
Orlando
ORD
Chicago
S$326 Return, found 2 days ago
S$326
Return
found 2 days ago
Select Delta flight, departing Sun, 14 Sep from Orlando to Chicago, returning Tue, 16 Sep, priced at S$326 found 2 days ago
Delta
Sat, 13 Sep - Tue, 16 Sep
MCO
Orlando
ORD
Chicago
S$332 Return, found 3 days ago
S$332
Return
found 3 days ago
Select Delta flight, departing Sat, 13 Sep from Orlando to Chicago, returning Tue, 16 Sep, priced at S$332 found 3 days ago
United
Sat, 20 Sep - Sun, 21 Sep
MCO
Orlando
ORD
Chicago
S$332 Return, found 5 days ago
S$332
Return
found 5 days ago
Select United flight, departing Sat, 20 Sep from Orlando to Chicago, returning Sun, 21 Sep, priced at S$332 found 5 days ago
American Airlines
Sat, 13 Sep - Tue, 16 Sep
MCO
Orlando
ORD
Chicago
S$333 Return, found 3 days ago
S$333
Return
found 3 days ago
Select American Airlines flight, departing Sat, 13 Sep from Orlando to Chicago, returning Tue, 16 Sep, priced at S$333 found 3 days ago
American Airlines
Sat, 13 Sep - Tue, 16 Sep
MCO
Orlando
ORD
Chicago
S$334 Return, found 3 days ago
S$334
Return
found 3 days ago
Select American Airlines flight, departing Sat, 13 Sep from Orlando to Chicago, returning Tue, 16 Sep, priced at S$334 found 3 days ago
American Airlines
Sun, 14 Sep - Tue, 16 Sep
MCO
Orlando
ORD
Chicago
S$351 Return, found 2 days ago
S$351
Return
found 2 days ago
Select American Airlines flight, departing Sun, 14 Sep from Orlando to Chicago, returning Tue, 16 Sep, priced at S$351 found 2 days ago
American Airlines
Sat, 13 Sep - Tue, 16 Sep
MCO
Orlando
ORD
Chicago
S$351 Return, found 3 days ago
S$351
Return
found 3 days ago
Select American Airlines flight, departing Sat, 13 Sep from Orlando to Chicago, returning Tue, 16 Sep, priced at S$351 found 3 days ago

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

February is typically the cheapest month to fly

From S$90 - S$510 per traveller.

Graph displaying average flight prices per month

Orlando to Chicago route information
Origin airport
Orlando Intl.
Destination airport
O'Hare Intl.
Return price
S$293
Distance
1610 km
Average flight time
2 hours 2 mins

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!

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$294. 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.

Explore a world of travel with Expedia

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