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Cheap flights from Chicago to Orlando from $37

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Orlando departing on 1/19. 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 Chicago to Orlando

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Orlando that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Orlando.

Cheap last minute flights

Planning a quick getaway from Chicago to Orlando? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Orlando, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Orlando

Find recent round-trip train or bus tickets from Chicago to Orlando.

All round-trip flight deals to Orlando

The cheapest plane tickets to Orlando found on KAYAK recently.
12:25 pm - 4:12 pmORD-MCO
2h 47mnonstop
1:59 pm - 4:10 pmMCO-ORD
3h 11mnonstop
$75Spirit Airlines
Find Deal
Sun, Jan 19 - Thu, Jan 23
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$75Frontier
Find Deal
Sun, Jan 19 - Fri, Jan 24
5:28 pm - 9:37 pmORD-MCO
3h 09mnonstop
6:37 pm - 8:57 pmMCO-ORD
3h 20mnonstop
$76Frontier
Find Deal
Mon, Jan 20 - Fri, Jan 24
11:33 am - 3:19 pmMDW-MCO
2h 46mnonstop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$76Frontier
Find Deal
Mon, Jan 20 - Fri, Jan 24
8:00 am - 4:09 pmORD-MCO
7h 09m1 stop
11:00 am - 3:43 pmMCO-ORD
5h 43m1 stop
$197Delta
Find Deal
Tue, Feb 11 - Sat, Feb 15
5:05 pm - 12:35 amMDW-MCO
6h 30m1 stop
6:15 am - 11:59 amMCO-MDW
6h 44m1 stop
$197Delta
Find Deal
Tue, Feb 11 - Tue, Feb 25
8:40 am - 2:00 pmMDW-MCO
4h 20m1 stop
4:25 pm - 8:55 pmMCO-MDW
5h 30m1 stop
$208Southwest
Find Deal
Sun, Feb 16 - Fri, Feb 21
7:00 am - 4:25 pmORD-MCO
8h 25m2 stops
8:30 pm - 10:20 amMCO-ORD
14h 50m1 stop
$214Southwest
Find Deal
Mon, Feb 3 - Fri, Feb 7
6:45 pm - 10:35 pmORD-MCO
2h 50mnonstop
5:42 pm - 7:45 pmMCO-ORD
3h 03mnonstop
$225American Airlines
Find Deal
Wed, Jan 29 - Tue, Feb 4
12:05 pm - 3:57 pmORD-MCO
2h 52mnonstop
7:34 pm - 9:44 pmMCO-ORD
3h 10mnonstop
$227United Airlines
Find Deal
Tue, Feb 11 - Sat, Feb 15
12:25 pm - 4:12 pmORD-MCO
2h 47mnonstop
$37Spirit Airlines
Find Deal
Sun, Jan 19
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
$37Frontier
Find Deal
Sun, Jan 19
7:00 pm - 10:40 pmMDW-MCO
2h 40mnonstop
$79Southwest
Find Deal
Sat, Feb 15
3:25 pm - 7:05 pmMDW-MCO
2h 40mnonstop
$95Southwest
Find Deal
Tue, Jan 28
8:06 am - 11:45 amORD-MCO
2h 39mnonstop
$96American Airlines
Find Deal
Tue, Mar 18
5:10 pm - 12:35 amORD-MCO
6h 25m1 stop
$99Delta
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Sat, Feb 8
12:44 pm - 8:39 pmMDW-MCO
6h 55m1 stop
$99Delta
Find Deal
Tue, Feb 18
1:10 pm - 5:02 pmORD-MCO
2h 52mnonstop
$114United Airlines
Find Deal
Tue, Feb 11
12:57 pm - 4:42 pmORD-MCO
2h 45mnonstop
$134American Airlines
Find Deal
Wed, Mar 19
12:05 pm - 3:57 pmORD-MCO
2h 52mnonstop
$154United Airlines
Find Deal
Tue, Jan 21
6:06 pm - 9:58 pmORD-MCO
2h 52mnonstop
9:12 am - 11:20 amMCO-ORD
3h 08mnonstop
$88Spirit Airlines
Find Deal
Mon, Jan 13 - Sat, Jan 18
6:06 pm - 9:58 pmORD-MCO
2h 52mnonstop
9:12 am - 11:20 amMCO-ORD
3h 08mnonstop
$95Spirit Airlines
Find Deal
Mon, Jan 13 - Fri, Jan 17
4:08 pm - 12:40 amMDW-MCO
7h 32m1 stop
4:56 pm - 11:29 pmMCO-MDW
7h 33m1 stop
$118Frontier
Find Deal
Thu, Jan 9 - Sat, Jan 18
11:33 am - 3:25 pmMDW-MCO
2h 52mnonstop
8:26 am - 10:28 amMCO-MDW
3h 02mnonstop
$125Frontier
Find Deal
Mon, Jan 13 - Mon, Jan 20
10:01 pm - 1:53 amORD-MCO
2h 52mnonstop
1:59 pm - 4:10 pmMCO-ORD
3h 11mnonstop
Fri, Jan 10 - Fri, Jan 17
12:25 pm - 4:12 pmORD-MCO
2h 47mnonstop
9:12 am - 8:17 pmMCO-ORD
12h 05m1 stop
Sun, Jan 12 - Sun, Jan 26
3:25 pm - 7:05 pmMDW-MCO
2h 40mnonstop
7:15 am - 9:10 amMCO-MDW
2h 55mnonstop
$337Southwest
Find Deal
Mon, Jan 13 - Thu, Jan 16
3:25 pm - 7:05 pmMDW-MCO
2h 40mnonstop
10:25 am - 12:20 pmMCO-MDW
2h 55mnonstop
$543Southwest
Find Deal
Thu, Jan 9 - Thu, Jan 23
3:41 pm - 9:40 pmMDW-MCO
4h 59m1 stop
11:45 am - 6:14 pmMCO-MDW
7h 29m1 stop
$757Delta
Find Deal
Sat, Jan 11 - Wed, Jan 15
3:41 pm - 9:40 pmMDW-MCO
4h 59m1 stop
5:30 am - 10:12 amMCO-MDW
5h 42m1 stop
$777Delta
Find Deal
Sat, Jan 11 - Thu, Jan 16
12:25 pm - 4:12 pmORD-MCO
2h 47mnonstop
1:59 pm - 4:10 pmMCO-ORD
3h 11mnonstop
$75Spirit Airlines
Find Deal
Sun, Jan 19 - Thu, Jan 23
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
12:38 pm - 2:42 pmMCO-MDW
3h 04mnonstop
$75Frontier
Find Deal
Sun, Jan 19 - Fri, Jan 24
5:28 pm - 9:37 pmORD-MCO
3h 09mnonstop
6:37 pm - 8:57 pmMCO-ORD
3h 20mnonstop
$76Frontier
Find Deal
Mon, Jan 20 - Fri, Jan 24
4:18 pm - 8:15 pmORD-MCO
2h 57mnonstop
1:59 pm - 4:10 pmMCO-ORD
3h 11mnonstop
Sun, Jan 26 - Tue, Feb 4
8:00 am - 11:50 amORD-MCO
2h 50mnonstop
6:37 pm - 8:57 pmMCO-ORD
3h 20mnonstop
Tue, Feb 4 - Fri, Feb 7
6:10 pm - 9:50 pmMDW-MCO
2h 40mnonstop
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
$179Southwest
Find Deal
Tue, Feb 4 - Thu, Feb 27
6:10 pm - 9:50 pmMDW-MCO
2h 40mnonstop
10:25 am - 12:20 pmMCO-MDW
2h 55mnonstop
$189Southwest
Find Deal
Tue, Jan 28 - Thu, Jan 30
6:45 pm - 10:35 pmORD-MCO
2h 50mnonstop
5:42 pm - 7:45 pmMCO-ORD
3h 03mnonstop
$225American Airlines
Find Deal
Wed, Jan 29 - Tue, Feb 4
12:05 pm - 3:57 pmORD-MCO
2h 52mnonstop
7:34 pm - 9:44 pmMCO-ORD
3h 10mnonstop
$227United Airlines
Find Deal
Tue, Feb 11 - Sat, Feb 15
6:10 am - 9:55 amORD-MCO
2h 45mnonstop
6:05 pm - 8:16 pmMCO-ORD
3h 11mnonstop
$239United Airlines
Find Deal
Sun, Feb 16 - Thu, Feb 20

Frontier flights from Chicago to Orlando

Our best Frontier deals on Chicago to Orlando flight tickets
Frontier
Jan 19
MDW10:58 amChicago Midway
2h 47m
MCO2:45 pmOrlando
Jan 24
MCO12:38 pmOrlando
3h 04m
MDW2:42 pmChicago Midway
Frontier
Jan 20
ORD5:28 pmChicago O'Hare Intl
3h 09m
MCO9:37 pmOrlando
Jan 24
MCO6:37 pmOrlando
3h 20m
ORD8:57 pmChicago O'Hare Intl
Frontier
Jan 20
MDW11:33 amChicago Midway
2h 46m
MCO3:19 pmOrlando
Jan 24
MCO12:38 pmOrlando
3h 04m
MDW2:42 pmChicago Midway

Spirit Airlines flights from Chicago to Orlando

Our best Spirit Airlines deals on Chicago to Orlando flight tickets
Spirit Airlines
Jan 19
ORD12:25 pmChicago O'Hare Intl
2h 47m
MCO4:12 pmOrlando
Jan 23
MCO1:59 pmOrlando
3h 11m
ORD4:10 pmChicago O'Hare Intl
Spirit Airlines
Jan 19
ORD6:06 pmChicago O'Hare Intl
2h 52m
MCO9:58 pmOrlando
Jan 23
MCO9:12 amOrlando
3h 08m
ORD11:20 amChicago O'Hare Intl
Spirit Airlines
Jan 23
ORD12:25 pmChicago O'Hare Intl
2h 47m
MCO4:12 pmOrlando
Jan 24
MCO9:12 amOrlando
3h 08m
ORD11:20 amChicago O'Hare Intl

See travel insights to Orlando from

How to get the cheapest flight ticket from Chicago to Orlando

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 typical price of a round-trip flight between Chicago and Orlando?

What is the cheapest month to fly to Orlando?

The month of May is, on average, the cheapest month to fly to Orlando from Chicago, with most prices found around $176. If you’re not able to fly to Orlando in May, then April is your next best option. Flight prices from Chicago to Orlando during April average around $184.

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

Our data shows that Tuesday is the least expensive day to fly to Orlando. Tickets to fly out on this day can be as low as $236. On the other hand, Monday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $315.

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

The cheapest time of day to fly to Orlando is in the afternoon when flights can be purchased for as low as $202. In contrast, the most expensive time of day to depart to Orlando is at noon when prices are around $289.

What is the cheapest Chicago to Orlando flight route?

Fly from Chicago Greater Rockford to Orlando Sanford Intl for the best Chicago - Orlando flight prices

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

In general, most travelers find the cheapest time to book a flight to Orlando is about 10 days prior to their departure date when tickets on average are $283. Keep in mind that you might be able to find cheaper flights to Orlando at any time. In fact, our users found flights for as low as $188 in the past 72 hours.

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

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

How have Chicago to Orlando flight prices changed over time?

As of January 2025, prices for Chicago to Orlando flights are approximately 93% more expensive when compared to flights at the same time last year.

Cheap Chicago to Orlando flight deals and tips

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

Best Price Found

$37

Fastest flight time

2h 29m

Direct flights

Tue, Wed, Thu, Fri, Sat and Sun

Airports in Orlando

2 airports
The best one-way flight to Orlando from Chicago in the past 72 hours is $37. The best round-trip flight deal from Chicago to Orlando found on momondo in the last 72 hours is $75.
The fastest flight from Chicago to Orlando takes 2h 29m
Direct flights go from Chicago to Orlando on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: Southwest, Allegiant Air and American Airlines.
There are 2 airports near Orlando: Orlando (MCO), Orlando Sanford Intl (SFB)

  • How far is Chicago to Orlando by plane?

    The straight-line distance from Chicago to Orlando is 985.3 mi. A reasonable flight in good conditions will take 2h 29m.

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

    Prices for flights from Chicago to Orlando refresh daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Orlando.

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

    The travel and health documents required for your trip to Orlando 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 Orlando. 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 Chicago to Orlando?

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


Best airlines flying from Chicago to Orlando

Compare and see reviews for airlines that fly from Chicago to Orlando with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $56Free CancellationRating
6.0
3,428 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $58Free CancellationRating
6.3
8,074 reviews
Search Spirit Airlines flights
Allegiant AirPriceFrom $112Free CancellationRating
7.3
799 reviews
Search Allegiant Air flights
United AirlinesPriceFrom $154Free CancellationRating
7.4
8,939 reviews
Search United Airlines flights
American AirlinesPriceFrom $177Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $196Free CancellationRating
8.0
8,499 reviews
Search Delta flights
SouthwestPriceFrom $246Free CancellationRating
8.1
4,649 reviews
Search Southwest flights
  • Southwest Flights From Chicago to Orlando

    Southwest flight deals from Chicago to Orlando start from $246 round-trip. Over the 41 Southwest flights for this route in a normal week, average airfare is usually $419 round-trip - but some users have found much cheaper deals with momondo.

  • United Airlines Flights From Chicago to Orlando

    United Airlines (7.4/10 from 8,939 reviews) operates around 31 flights from Chicago to Orlando in any given week. The average United Airlines airfare for this route is around $360, with deals from around $154 rare but found on momondo. Referenced prices are for round-trip Chicago to Orlando flight searches in the last 72 hours.


Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Orlando. momondo saves you time and could save you money on your trip.

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

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

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Orlando from Chicago.

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

Yes momondo offers price alerts on flights to Orlando from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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Find better results for your trip to the United States

Fly into one of these airports located in Orlando

Airports listed have a maximum distance of 18.3 mi from Orlando