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Cheap flights from Orlando to Chicago from $50

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Orlando to Chicago departing on 10/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Frontier Logo
5:24 pm - 7:44 pmMCO-ORD
3h 20mnonstop
Frontier Logo
8:49 pm - 12:35 amORD-MCO
2h 46mnonstop
$87Frontier
Find Deal
Thu, Oct 2 - Sun, Oct 5
Frontier Logo
5:24 pm - 7:44 pmMCO-ORD
3h 20mnonstop
Frontier Logo
8:49 pm - 12:35 amORD-MCO
2h 46mnonstop
$88Frontier
Find Deal
Fri, Oct 3 - Mon, Oct 6
Frontier Logo
1:02 pm - 3:17 pmMCO-ORD
3h 15mnonstop
Frontier Logo
8:49 pm - 12:35 amORD-MCO
2h 46mnonstop
$89Frontier
Find Deal
Sat, Sep 27 - Mon, Sep 29
Logo
6:05 am - 8:14 amMCO-ORD
3h 09mnonstop
Logo
6:58 pm - 10:50 pmORD-MCO
2h 52mnonstop
$90
Find Deal
Thu, Oct 9 - Tue, Oct 14
Frontier Logo
5:24 pm - 7:44 pmMCO-ORD
3h 20mnonstop
Frontier Logo
8:49 pm - 12:35 amORD-MCO
2h 46mnonstop
$91Frontier
Find Deal
Fri, Sep 26 - Mon, Sep 29
Frontier Logo
5:24 pm - 7:44 pmMCO-ORD
3h 20mnonstop
Frontier Logo
8:00 am - 11:57 amORD-MCO
2h 57mnonstop
$92Frontier
Find Deal
Fri, Oct 3 - Sat, Oct 4
Frontier Logo
5:24 pm - 7:44 pmMCO-ORD
3h 20mnonstop
Frontier Logo
8:49 pm - 12:35 amORD-MCO
2h 46mnonstop
$93Frontier
Find Deal
Fri, Sep 26 - Mon, Sep 29
Spirit Airlines Logo
7:50 pm - 9:58 pmMCO-ORD
3h 08mnonstop
Spirit Airlines Logo
6:00 am - 9:44 amORD-MCO
2h 44mnonstop
$98Spirit Airlines
Find Deal
Tue, Sep 30 - Tue, Oct 7
Spirit Airlines Logo
7:30 pm - 9:33 pmMCO-ORD
3h 03mnonstop
Spirit Airlines Logo
7:51 pm - 11:43 pmORD-MCO
2h 52mnonstop
$99Spirit Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 13
Spirit Airlines Logo
7:50 pm - 9:58 pmMCO-ORD
3h 08mnonstop
Spirit Airlines Logo
5:17 pm - 9:06 pmORD-MCO
2h 49mnonstop
$104Spirit Airlines
Find Deal
Fri, Sep 26 - Mon, Sep 29

Frontier flights from Orlando to Chicago O'Hare Intl Airport

Our best Frontier deals on Orlando to Chicago O'Hare Intl Airport flight tickets
Frontier
Oct 2
MCO5:24 pmOrlando
3h 20m
ORD7:44 pmChicago O'Hare Intl
Oct 5
ORD8:49 pmChicago O'Hare Intl
2h 46m
MCO12:35 amOrlando
$87
Find similar
Frontier
Oct 3
MCO5:24 pmOrlando
3h 20m
ORD7:44 pmChicago O'Hare Intl
Oct 6
ORD8:49 pmChicago O'Hare Intl
2h 46m
MCO12:35 amOrlando
$88
Find similar
Frontier
Sep 27
MCO1:02 pmOrlando
3h 15m
ORD3:17 pmChicago O'Hare Intl
Sep 29
ORD8:49 pmChicago O'Hare Intl
2h 46m
MCO12:35 amOrlando
$89
Find similar

Spirit Airlines flights from Orlando to Chicago O'Hare Intl Airport

Our best Spirit Airlines deals on Orlando to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Sep 30
MCO7:50 pmOrlando
3h 08m
ORD9:58 pmChicago O'Hare Intl
Oct 7
ORD6:00 amChicago O'Hare Intl
2h 44m
MCO9:44 amOrlando
$98
Find similar
Spirit Airlines
Oct 9
MCO7:30 pmOrlando
3h 03m
ORD9:33 pmChicago O'Hare Intl
Oct 13
ORD7:51 pmChicago O'Hare Intl
2h 52m
MCO11:43 pmOrlando
$99
Find similar
Spirit Airlines
Sep 25
MCO2:07 pmOrlando
3h 05m
ORD4:12 pmChicago O'Hare Intl
Sep 29
ORD6:30 amChicago O'Hare Intl
2h 43m
MCO10:13 amOrlando
$100
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Orlando to Chicago O'Hare Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Orlando to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 10/2

5:24 pm-7:44 pm

Nonstop3h 20m

Chicago O'Hare Intl

Sun 10/5

8:49 pm-12:35 am

Nonstop2h 46m

$87

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 10/3

5:24 pm-7:44 pm

Nonstop3h 20m

Chicago O'Hare Intl

Mon 10/6

8:49 pm-12:35 am

Nonstop2h 46m

$88

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 9/27

1:02 pm-3:17 pm

Nonstop3h 15m

Chicago O'Hare Intl

Mon 9/29

8:49 pm-12:35 am

Nonstop2h 46m

$89

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 10/9

6:05 am-8:14 am

Nonstop3h 09m

Chicago O'Hare Intl

Tue 10/14

6:58 pm-10:50 pm

Nonstop2h 52m

$90

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 9/26

5:24 pm-7:44 pm

Nonstop3h 20m

Chicago O'Hare Intl

Mon 9/29

8:49 pm-12:35 am

Nonstop2h 46m

$91

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 10/3

5:24 pm-7:44 pm

Nonstop3h 20m

Chicago O'Hare Intl

Sat 10/4

8:00 am-11:57 am

Nonstop2h 57m

$92

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 9/26

5:24 pm-7:44 pm

Nonstop3h 20m

Chicago O'Hare Intl

Mon 9/29

8:49 pm-12:35 am

Nonstop2h 46m

$93

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 9/30

7:50 pm-9:58 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 10/7

6:00 am-9:44 am

Nonstop2h 44m

$98

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 10/9

7:30 pm-9:33 pm

Nonstop3h 03m

Chicago O'Hare Intl

Mon 10/13

7:51 pm-11:43 pm

Nonstop2h 52m

$99

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 9/26

7:50 pm-9:58 pm

Nonstop3h 08m

Chicago O'Hare Intl

Mon 9/29

5:17 pm-9:06 pm

Nonstop2h 49m

$104

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Orlando to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Orlando averaging around $162.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $262. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Orlando because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $589.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Orlando in the evening is the least expensive time of day to depart. momondo users have found prices as low as $230 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $708. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Orlando to Chicago O'Hare Intl flight route?

Fly from Orlando to Chicago O'Hare Intl for the best Orlando - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Orlando when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $220 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Orlando for as low as $176 on momondo.

What cabin class options are available on Orlando to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Orlando to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Orlando to Chicago O'Hare Intl Airport flight prices changed over time?

As of September 2025, prices for Orlando to Chicago O'Hare Intl Airport flights are approximately 63% more expensive when compared to flights at the same time last year.

When to book flights from Orlando to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Orlando to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Orlando to Chicago O'Hare Intl Airport (ORL to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Orlando to Chicago O'Hare Intl Airport

Best Price Found

$111

Fastest flight time

3h 00m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Orlando in the past 72 hours is $111. The best round-trip flight deal from Orlando to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $170.
The fastest flight from Orlando to Chicago O'Hare Intl Airport takes 3h 00m
Direct flights go from Orlando to Chicago O'Hare Intl Airport every day.
Search flight deals

  • How far is Orlando to Chicago O'Hare Intl by plane?

    A flight from Orlando to Chicago O'Hare Intl will travel around 997.5 mi. 3h 00m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Orlando to Chicago O'Hare Intl Airport?

    Prices for flights from Orlando to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Orlando to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Orlando to Chicago O'Hare Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Orlando to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Orlando to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Orlando to Chicago O'Hare Intl Airport?

Best airlines flying from Orlando to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Orlando to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $70Free CancellationRating
5.8
3,172 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $73Free CancellationRating
6.3
8,015 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $158Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $159Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
DeltaPriceFrom $276Free CancellationRating
7.9
7,954 reviews
Search Delta flights

  • Southwest Flights From Orlando to Chicago O'Hare Intl Airport

    Across 14 Southwest flights from Orlando to Chicago O'Hare Intl Airport this week, the average price was $286, with the best Southwest deals starting from $159 round-trip. 4,242 users have rated Southwest on momondo, with an average score of 8.0/10.

  • United Airlines Flights From Orlando to Chicago O'Hare Intl Airport

    Across 8,929 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Orlando to Chicago O'Hare Intl Airport about 62 times each week, with ticket deals ranging from $158 to $344. Price data is based on momondo searches in the last 72 hours.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
Aurora
Janesville
Benton Harbor

Why use momondo?

Why should I use momondo to find a flight deal from Orlando to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Orlando to Chicago for you.

Can I find flights from Orlando to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Orlando on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Orlando to Chicago?

momondo helps you find the best flight between Orlando and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Orlando to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Orlando to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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