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Cheap flights from Orlando Airport to Chicago from $53

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 Airport to Chicago departing on 8/23. 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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Find the cheapest flights from Orlando Airport to Chicago

Cheap round-trip flights

Logo
6:31 am - 10:52 amMCO-ORD
5h 21m1 stop
Logo
8:49 pm - 12:35 amORD-MCO
2h 46mnonstop
$98
Find Deal
Tue, Sep 16 - Sun, Sep 21
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
Frontier Logo
10:51 am - 2:33 pmMDW-MCO
2h 42mnonstop
$98Frontier
Find Deal
Fri, Sep 12 - Sat, Sep 13
Frontier Logo
1:02 pm - 3:17 pmMCO-ORD
3h 15mnonstop
Frontier Logo
8:49 pm - 12:35 amORD-MCO
2h 46mnonstop
$99Frontier
Find Deal
Sat, Sep 6 - Sun, Sep 7
Frontier Logo
7:25 am - 9:18 amMCO-MDW
2h 53mnonstop
Frontier Logo
10:13 am - 1:55 pmMDW-MCO
2h 42mnonstop
$99Frontier
Find Deal
Sun, Sep 14 - Sun, Sep 21
Logo
7:50 pm - 9:58 pmMCO-ORD
3h 08mnonstop
Logo
8:49 pm - 12:35 amORD-MCO
2h 46mnonstop
$100
Find Deal
Wed, Sep 17 - Fri, Sep 19
Frontier Logo
6:35 am - 8:32 amMCO-MDW
2h 57mnonstop
Frontier Logo
9:32 am - 1:14 pmMDW-MCO
2h 42mnonstop
$100Frontier
Find Deal
Fri, Oct 31 - Mon, Nov 3
Spirit Airlines Logo
7:50 pm - 9:58 pmMCO-ORD
3h 08mnonstop
Spirit Airlines Logo
6:30 am - 10:13 amORD-MCO
2h 43mnonstop
$101Spirit Airlines
Find Deal
Fri, Sep 5 - Sun, Sep 7
Logo
1:02 pm - 3:17 pmMCO-ORD
3h 15mnonstop
Logo
6:00 am - 9:44 amORD-MCO
2h 44mnonstop
$102
Find Deal
Sat, Sep 20 - Wed, Oct 8
Spirit Airlines Logo
7:50 pm - 9:58 pmMCO-ORD
3h 08mnonstop
Spirit Airlines Logo
6:30 am - 10:13 amORD-MCO
2h 43mnonstop
$108Spirit Airlines
Find Deal
Tue, Sep 16 - Wed, Sep 24
Spirit Airlines Logo
7:50 pm - 9:58 pmMCO-ORD
3h 08mnonstop
Spirit Airlines Logo
6:30 am - 10:13 amORD-MCO
2h 43mnonstop
$111Spirit Airlines
Find Deal
Tue, Sep 16 - Thu, Sep 25

Frontier flights from Orlando Airport to Chicago

Our best Frontier deals on Orlando Airport to Chicago flight tickets
Frontier
Sep 12
MCO7:00 amOrlando
2h 53m
MDW8:53 amChicago Midway
Sep 13
MDW10:51 amChicago Midway
2h 42m
MCO2:33 pmOrlando
$98
Find similar
Frontier
Sep 6
MCO1:02 pmOrlando
3h 15m
ORD3:17 pmChicago O'Hare Intl
Sep 7
ORD8:49 pmChicago O'Hare Intl
2h 46m
MCO12:35 amOrlando
$99
Find similar
Frontier
Oct 31
MCO6:35 amOrlando
2h 57m
MDW8:32 amChicago Midway
Nov 3
MDW9:32 amChicago Midway
2h 42m
MCO1:14 pmOrlando
$100
Find similar

Spirit Airlines flights from Orlando Airport to Chicago

Our best Spirit Airlines deals on Orlando Airport to Chicago flight tickets
Spirit Airlines
Aug 23
MCO2:07 pmOrlando
3h 03m
ORD4:10 pmChicago O'Hare Intl
Aug 25
ORD5:16 pmChicago O'Hare Intl
2h 45m
MCO9:01 pmOrlando
$99
Find similar
Spirit Airlines
Sep 5
MCO7:50 pmOrlando
3h 08m
ORD9:58 pmChicago O'Hare Intl
Sep 7
ORD6:30 amChicago O'Hare Intl
2h 43m
MCO10:13 amOrlando
$101
Find similar
Spirit Airlines
Sep 16
MCO7:50 pmOrlando
3h 08m
ORD9:58 pmChicago O'Hare Intl
Sep 24
ORD6:30 amChicago O'Hare Intl
2h 43m
MCO10:13 amOrlando
$108
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Orlando Airport to Chicago 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 August 18, 2025.
Use the filters below to find and compare flights from Orlando Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 9/16

6:31 am-10:52 am

1 stop5h 21m

Chicago O'Hare Intl

Sun 9/21

8:49 pm-12:35 am

Nonstop2h 46m

$98

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 9/12

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

Sat 9/13

10:51 am-2:33 pm

Nonstop2h 42m

$98

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 9/6

1:02 pm-3:17 pm

Nonstop3h 15m

Chicago O'Hare Intl

Sun 9/7

8:49 pm-12:35 am

Nonstop2h 46m

$99

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sun 9/14

7:25 am-9:18 am

Nonstop2h 53m

Chicago Midway

Sun 9/21

10:13 am-1:55 pm

Nonstop2h 42m

$99

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 9/17

7:50 pm-9:58 pm

Nonstop3h 08m

Chicago O'Hare Intl

Fri 9/19

8:49 pm-12:35 am

Nonstop2h 46m

$100

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 10/31

6:35 am-8:32 am

Nonstop2h 57m

Chicago Midway

Mon 11/3

9:32 am-1:14 pm

Nonstop2h 42m

$100

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 9/5

7:50 pm-9:58 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 9/7

6:30 am-10:13 am

Nonstop2h 43m

$101

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 9/20

1:02 pm-3:17 pm

Nonstop3h 15m

Chicago O'Hare Intl

Wed 10/8

6:00 am-9:44 am

Nonstop2h 44m

$102

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 9/16

7:50 pm-9:58 pm

Nonstop3h 08m

Chicago O'Hare Intl

Wed 9/24

6:30 am-10:13 am

Nonstop2h 43m

$108

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 9/16

7:50 pm-9:58 pm

Nonstop3h 08m

Chicago O'Hare Intl

Thu 9/25

6:30 am-10:13 am

Nonstop2h 43m

$111

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 Airport to Chicago

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?

The month of September is, on average, the cheapest month to fly to Chicago from Orlando Airport, with most prices found around $136. If you’re not able to fly to Chicago in September, then February is your next best option. Flight prices from Orlando Airport to Chicago during February average around $152.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $234. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Orlando Airport to Chicago for around $462.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Orlando Airport to Chicago during this time can be as low as $220. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $567.

What is the cheapest Orlando to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Orlando Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $217 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Orlando Airport for as low as $167 on momondo.

What cabin class options are available on Orlando to Chicago flights?

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

How have Orlando Airport to Chicago flight prices changed over time?

As of August 2025, prices for Orlando Airport to Chicago flights are approximately 5% more expensive when compared to flights at the same time last year.

When to book flights from Orlando Airport to Chicago

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

Cheap Orlando Airport to Chicago (MCO to CHI) flight deals and tips

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

Best Price Found

$53

Fastest flight time

2h 45m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Orlando Airport in the past 72 hours is $53. The best round-trip flight deal from Orlando Airport to Chicago found on momondo in the last 72 hours is $98.
The fastest flight from Orlando Airport to Chicago takes 2h 45m
Direct flights go from Orlando Airport to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • How far is Orlando to Chicago by plane?

    There are 993.7 mi between Orlando and Chicago. A reasonable flight in good conditions will take 2h 51m.

  • When did momondo last update prices for flights from Orlando Airport to Chicago?

    Prices for flights from Orlando Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Orlando Airport to Chicago?

  • How old do you have to be to fly from Orlando Airport to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Orlando Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Orlando Airport to Chicago?

  • What is the most popular airline from Orlando Airport to Chicago?

Best airlines flying from Orlando Airport to Chicago

Compare and see reviews for airlines that fly from Orlando Airport to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $72Free CancellationRating
5.8
3,212 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $72Free CancellationRating
6.3
8,038 reviews
Search Spirit Airlines flights
DeltaPriceFrom $114Free CancellationRating
8.0
7,981 reviews
Search Delta flights
United AirlinesPriceFrom $158Free CancellationRating
7.4
8,925 reviews
Search United Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $159Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

  • Southwest Flights From Orlando Airport to Chicago

    Across 64 Southwest flights from Orlando Airport to Chicago this week, the average price was $317, with the best Southwest deals starting from $159 round-trip. 4,246 users have rated Southwest on momondo, with an average score of 8.0/10.

  • United Airlines Flights From Orlando Airport to Chicago

    Another popular option for Orlando Airport to Chicago flights is United Airlines (7.4/10, 8,925 ratings). United Airlines flies from Orlando Airport to Chicago around 18 times per week, with deals starting from $158 round-trip and rising to an average price of around $341.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

Finding the right flight to Chicago from Orlando is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

All flight searches from Orlando to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Chicago from Orlando. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Chicago from Orlando are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport