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Cheap flights from Orlando Airport to Chicago from $39

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 5/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Orlando Airport to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Orlando Airport to Chicago.
Frontier Logo
9:57 pm - 12:04 amMCO-ORD
3h 07mnonstop
Frontier Logo
5:14 pm - 9:11 pmORD-MCO
2h 57mnonstop
$86Frontier
Find Deal
Sat, May 24 - Sun, May 25
Frontier Logo
10:17 pm - 12:20 amMCO-ORD
3h 03mnonstop
Frontier Logo
9:17 am - 1:11 pmORD-MCO
2h 54mnonstop
$87Frontier
Find Deal
Thu, May 22 - Sun, May 25
Spirit Airlines Logo
9:25 pm - 11:29 pmMCO-ORD
3h 04mnonstop
Spirit Airlines Logo
7:47 am - 11:26 amORD-MCO
2h 39mnonstop
$109Spirit Airlines
Find Deal
Sat, May 10 - Tue, May 13
Spirit Airlines Logo
9:25 pm - 11:29 pmMCO-ORD
3h 04mnonstop
Spirit Airlines Logo
12:41 pm - 8:37 pmORD-MCO
6h 56m1 stop
$113Spirit Airlines
Find Deal
Fri, May 9 - Wed, May 14
Southwest Logo
11:00 am - 1:05 pmMCO-ORD
3h 05mnonstop
Southwest Logo
6:00 am - 9:40 amORD-MCO
2h 40mnonstop
$178Southwest
Find Deal
Wed, May 21 - Sun, May 25
Southwest Logo
3:55 pm - 5:45 pmMCO-MDW
2h 50mnonstop
Southwest Logo
8:25 am - 12:05 pmMDW-MCO
2h 40mnonstop
$179Southwest
Find Deal
Sat, May 24 - Sun, May 25
American Airlines Logo
6:52 am - 8:59 amMCO-ORD
3h 07mnonstop
American Airlines Logo
11:35 am - 3:16 pmORD-MCO
2h 41mnonstop
$192American Airlines
Find Deal
Wed, May 28 - Wed, May 28
Delta Logo
2:00 pm - 6:48 pmMCO-ORD
5h 48m1 stop
Delta Logo
10:30 am - 6:54 pmORD-MCO
7h 24m1 stop
$199Delta
Find Deal
Sat, May 24 - Sun, May 25
American Airlines Logo
6:00 am - 8:12 amMCO-ORD
3h 12mnonstop
American Airlines Logo
7:00 pm - 10:50 pmORD-MCO
2h 50mnonstop
$208American Airlines
Find Deal
Thu, Jul 3 - Sun, Jul 6
Delta Logo
6:15 am - 9:40 amMCO-MDW
4h 25m1 stop
Delta Logo
12:48 pm - 6:32 pmMDW-MCO
4h 44m1 stop
$208Delta
Find Deal
Sun, May 25 - Wed, May 28

Spirit Airlines flights from Orlando Airport to Chicago

Our best Spirit Airlines deals on Orlando Airport to Chicago flight tickets
Spirit Airlines
May 1
MCO6:00 amOrlando
3h 04m
ORD8:04 amChicago O'Hare Intl
May 5
ORD5:07 pmChicago O'Hare Intl
2h 50m
MCO8:57 pmOrlando
Spirit Airlines
May 10
MCO9:25 pmOrlando
3h 04m
ORD11:29 pmChicago O'Hare Intl
May 13
ORD7:47 amChicago O'Hare Intl
2h 39m
MCO11:26 amOrlando
Spirit Airlines
May 9
MCO9:25 pmOrlando
3h 04m
ORD11:29 pmChicago O'Hare Intl
May 14
ORD12:41 pmChicago O'Hare Intl
6h 56m
1 stop
MCO8:37 pmOrlando

American Airlines flights from Orlando Airport to Chicago

Our best American Airlines deals on Orlando Airport to Chicago flight tickets
American Airlines
May 28
MCO6:52 amOrlando
3h 07m
ORD8:59 amChicago O'Hare Intl
May 28
ORD11:35 amChicago O'Hare Intl
2h 41m
MCO3:16 pmOrlando
American Airlines
Jul 3
MCO6:00 amOrlando
3h 12m
ORD8:12 amChicago O'Hare Intl
Jul 6
ORD7:00 pmChicago O'Hare Intl
2h 50m
MCO10:50 pmOrlando
American Airlines
Jul 3
MCO6:00 amOrlando
3h 12m
ORD8:12 amChicago O'Hare Intl
Jul 7
ORD6:57 amChicago O'Hare Intl
5h 15m
1 stop
MCO1:12 pmOrlando

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 $146. If you’re not able to fly to Chicago in September, then April is your next best option. Flight prices from Orlando Airport to Chicago during April average around $150.

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 $235. 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 $503.

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 $158. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $720.

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 13 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $220 when searching 13 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 $156 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 April 2025, prices for Orlando Airport to Chicago flights are approximately 18% cheaper 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

$39

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 $39. The best round-trip flight deal from Orlando Airport to Chicago found on momondo in the last 72 hours is $86.
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)

  • 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 45m.

  • 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 $64Free CancellationRating
5.9
3,283 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $70Free CancellationRating
6.3
7,940 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $157Free CancellationRating
7.4
8,684 reviews
Search United Airlines flights
American AirlinesPriceFrom $161Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $184Free CancellationRating
8.0
4,286 reviews
Search Southwest flights
DeltaPriceFrom $227Free CancellationRating
8.0
7,920 reviews
Search Delta flights
  • Southwest Flights From Orlando Airport to Chicago

    Across 57 Southwest flights from Orlando Airport to Chicago this week, the average price was $388, with the best Southwest deals starting from $184 round-trip. 4,286 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, 8,684 ratings). United Airlines flies from Orlando Airport to Chicago around 32 times per week, with deals starting from $157 round-trip and rising to an average price of around $329.


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
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
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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Sun 4/27
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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