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Cheap flights from Orlando to Chicago Midway Airport from $56

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 Midway Airport departing on 12/5. 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 to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Orlando to Chicago 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 Orlando to Chicago.

Cheap last minute flights

Planning a quick getaway from Orlando to Chicago? 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 Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Orlando to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
5:15 am - 10:09 amMCO-MDW
5h 54m1 stop
10:08 am - 1:49 pmMDW-MCO
2h 41mnonstop
$106Frontier
Find Deal
Wed, Feb 26 - Sat, Mar 1
10:39 am - 6:26 pmMCO-MDW
8h 47m1 stop
4:41 pm - 1:46 amMDW-MCO
8h 05m1 stop
$108Frontier
Find Deal
Thu, Jan 16 - Mon, Jan 20
12:38 pm - 2:33 pmMCO-MDW
2h 55mnonstop
4:35 pm - 12:40 amMDW-MCO
7h 05m1 stop
$110Frontier
Find Deal
Fri, Jan 10 - Mon, Jan 13
10:39 am - 6:26 pmMCO-MDW
8h 47m1 stop
10:58 am - 2:45 pmMDW-MCO
2h 47mnonstop
$111Frontier
Find Deal
Thu, Jan 16 - Sun, Jan 19
11:56 am - 1:54 pmMCO-MDW
2h 58mnonstop
12:36 pm - 11:58 pmMDW-MCO
10h 22m1 stop
$112Frontier
Find Deal
Fri, Dec 6 - Mon, Dec 9
11:56 am - 1:54 pmMCO-MDW
2h 58mnonstop
10:58 am - 2:47 pmMDW-MCO
2h 49mnonstop
$113Frontier
Find Deal
Fri, Dec 6 - Sun, Dec 8
11:56 am - 1:54 pmMCO-MDW
2h 58mnonstop
10:58 am - 2:47 pmMDW-MCO
2h 49mnonstop
$114Frontier
Find Deal
Fri, Dec 6 - Sun, Dec 8
5:34 pm - 11:29 pmMCO-MDW
6h 55m1 stop
4:41 pm - 1:46 amMDW-MCO
8h 05m1 stop
$115Frontier
Find Deal
Sat, Jan 18 - Mon, Jan 20
11:56 am - 1:54 pmMCO-MDW
2h 58mnonstop
10:58 am - 2:47 pmMDW-MCO
2h 49mnonstop
$116Frontier
Find Deal
Fri, Dec 6 - Sun, Dec 8
10:25 am - 12:15 pmMCO-MDW
2h 50mnonstop
8:00 pm - 11:40 pmMDW-MCO
2h 40mnonstop
$264Southwest
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Wed, Dec 4 - Sun, Dec 8
2:36 pm - 10:45 pmMCO-MDW
9h 09m1 stop
$56Frontier
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Thu, Dec 5
7:35 am - 9:31 amMCO-MDW
2h 56mnonstop
$57Frontier
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Fri, Dec 20
3:40 pm - 5:35 pmMCO-MDW
2h 55mnonstop
$79Southwest
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Tue, Jan 14
7:50 pm - 9:45 pmMCO-MDW
2h 55mnonstop
$99Southwest
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Thu, Jan 9
6:00 pm - 10:06 pmMCO-MDW
5h 06m1 stop
$108Delta
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Fri, Dec 13
5:30 am - 9:50 amMCO-MDW
5h 20m1 stop
$128Delta
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Wed, Dec 4
8:00 am - 8:31 amMCO-MDW
25h 31m2 stops
Sat, Jan 18
8:00 am - 8:31 amMCO-MDW
25h 31m2 stops
Wed, Jan 8
4:50 pm - 11:10 amMCO-MDW
19h 20m2 stops
$223Porter Airlines
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Tue, Dec 17
4:50 pm - 11:10 amMCO-MDW
19h 20m2 stops
$224Porter Airlines
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Tue, Dec 17
8:00 pm - 11:55 pmMCO-MDW
4h 55m1 stop
8:50 am - 12:39 pmMDW-MCO
2h 49mnonstop
$222Frontier
Find Deal
Mon, Nov 18 - Thu, Nov 21
5:05 am - 11:56 amMCO-MDW
7h 51m1 stop
9:00 am - 12:49 pmMDW-MCO
2h 49mnonstop
$234Frontier
Find Deal
Sun, Nov 17 - Sun, Nov 24
8:00 pm - 11:55 pmMCO-MDW
4h 55m1 stop
9:05 am - 12:54 pmMDW-MCO
2h 49mnonstop
$238Frontier
Find Deal
Mon, Nov 18 - Fri, Nov 22
8:38 am - 2:24 pmMCO-MDW
6h 46m1 stop
4:51 pm - 9:43 amMDW-MCO
15h 52m2 stops
Fri, Nov 15 - Mon, Nov 18
8:38 am - 2:24 pmMCO-MDW
6h 46m1 stop
4:51 pm - 9:43 amMDW-MCO
15h 52m2 stops
Fri, Nov 15 - Mon, Nov 18
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
8:00 pm - 11:40 pmMDW-MCO
2h 40mnonstop
$583Southwest
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Tue, Nov 19 - Sun, Nov 24
9:00 am - 12:50 pmMCO-MDW
4h 50m1 stop
11:50 am - 3:25 pmMDW-MCO
2h 35mnonstop
$588Southwest
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Tue, Nov 19 - Tue, Nov 26
6:15 am - 9:32 amMCO-MDW
4h 17m1 stop
6:00 am - 12:52 pmMDW-MCO
5h 52m1 stop
$636Delta
Find Deal
Tue, Nov 19 - Tue, Nov 26
6:15 am - 9:32 amMCO-MDW
4h 17m1 stop
9:31 am - 4:54 pmMDW-MCO
6h 23m1 stop
$717Delta
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Tue, Nov 19 - Thu, Nov 21
2:32 pm - 8:45 amMCO-MDW
19h 13m1 stop
7:55 pm - 3:14 pmMDW-MCO
18h 19m2 stops
$1,007Volaris
Find Deal
Mon, Nov 18 - Wed, Nov 20
6:10 am - 8:05 amMCO-MDW
2h 55mnonstop
9:00 am - 12:49 pmMDW-MCO
2h 49mnonstop
$107Frontier
Find Deal
Sat, Nov 23 - Sun, Nov 24
6:15 am - 8:10 amMCO-MDW
2h 55mnonstop
9:00 am - 12:49 pmMDW-MCO
2h 49mnonstop
$108Frontier
Find Deal
Fri, Nov 22 - Sun, Nov 24
6:00 am - 7:55 amMCO-MDW
2h 55mnonstop
9:00 am - 12:49 pmMDW-MCO
2h 49mnonstop
$109Frontier
Find Deal
Thu, Nov 21 - Sun, Nov 24
11:56 am - 1:54 pmMCO-MDW
2h 58mnonstop
10:58 am - 2:47 pmMDW-MCO
2h 49mnonstop
$113Frontier
Find Deal
Fri, Dec 6 - Sun, Dec 8
11:56 am - 1:54 pmMCO-MDW
2h 58mnonstop
11:33 am - 3:25 pmMDW-MCO
2h 52mnonstop
$114Frontier
Find Deal
Fri, Dec 6 - Mon, Dec 9
11:56 am - 1:54 pmMCO-MDW
2h 58mnonstop
11:33 am - 3:25 pmMDW-MCO
2h 52mnonstop
$117Frontier
Find Deal
Fri, Dec 6 - Mon, Dec 9
6:15 am - 8:10 amMCO-MDW
2h 55mnonstop
9:00 am - 12:49 pmMDW-MCO
2h 49mnonstop
$119Frontier
Find Deal
Fri, Nov 22 - Sun, Nov 24
6:00 am - 7:55 amMCO-MDW
2h 55mnonstop
10:58 am - 2:47 pmMDW-MCO
2h 49mnonstop
$123Frontier
Find Deal
Mon, Nov 25 - Sun, Dec 8
10:25 am - 12:15 pmMCO-MDW
2h 50mnonstop
7:15 pm - 10:55 pmMDW-MCO
2h 40mnonstop
$218Southwest
Find Deal
Wed, Dec 4 - Tue, Dec 10
6:25 am - 8:20 amMCO-MDW
2h 55mnonstop
8:00 pm - 11:40 pmMDW-MCO
2h 40mnonstop
$238Southwest
Find Deal
Sat, Dec 14 - Sun, Dec 15

Frontier flights from Orlando to Chicago Midway Airport

Our best Frontier deals on Orlando to Chicago Midway Airport flight tickets
Frontier
Feb 26
MCO5:15 amOrlando
5h 54m
1 stop
MDW10:09 amChicago Midway
Mar 1
MDW10:08 amChicago Midway
2h 41m
MCO1:49 pmOrlando
Frontier
Nov 23
MCO6:10 amOrlando
2h 55m
MDW8:05 amChicago Midway
Nov 24
MDW9:00 amChicago Midway
2h 49m
MCO12:49 pmOrlando
Frontier
Jan 16
MCO10:39 amOrlando
8h 47m
1 stop
MDW6:26 pmChicago Midway
Jan 20
MDW4:41 pmChicago Midway
8h 05m
1 stop
MCO1:46 amOrlando

Southwest flights from Orlando to Chicago Midway Airport

Our best Southwest deals on Orlando to Chicago Midway Airport flight tickets
Southwest
Dec 4
MCO10:25 amOrlando
2h 50m
MDW12:15 pmChicago Midway
Dec 8
MDW8:00 pmChicago Midway
2h 40m
MCO11:40 pmOrlando
Southwest
Nov 20
MCO10:25 amOrlando
2h 50m
MDW12:15 pmChicago Midway
Nov 23
MDW8:35 pmChicago Midway
2h 40m
MCO12:15 amOrlando
Southwest
Nov 19
MCO7:10 amOrlando
2h 55m
MDW9:05 amChicago Midway
Nov 24
MDW8:00 pmChicago Midway
2h 40m
MCO11:40 pmOrlando

How to get the cheapest flight ticket from Orlando to Chicago Midway 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 from Orlando to Chicago Midway Airport?

April. The cheapest time of year to fly to Chicago Midway Airport from Orlando is April. Most expensive is July

What is the cheapest day to depart Orlando for Chicago Midway Airport?

Friday. The cheapest day of the week is typically Friday. The most expensive is typically Monday

When is the cheapest time to fly from Orlando to Chicago Midway Airport?

At noon. Orlando to Chicago Midway Airport flights are approximately 10% more expensive in the evening than at noon

What is the cheapest airline that flies to Chicago Midway Airport from Orlando?

Frontier. Frontier, Southwest, and Delta are the most popular carriers operating from Orlando to Chicago Midway Airport

How far in advance should you book Orlando to Chicago Midway Airport flights?

57 days before. The cheapest time to buy a flight from Orlando to Chicago Midway Airport is approximately 57 days to departure

How many flights depart from Orlando to Chicago Midway Airport on average per day?

As of November 2024, 7 flights take off from Orlando and land in Chicago Midway Airport each day. The most common flight departure time for this route is 8:00AM, with 50% of daily flights taking off at noon.

How many flights depart from Orlando to Chicago Midway Airport on average per week?

As of November 2024, 54 flights take off from Orlando and land in Chicago Midway Airport each week. The most common flight departure day for this route is Thursday, with 19% of weekly flights taking off on this day.

Can stopping save me money on Orlando to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Orlando to Chicago Midway Airport.

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

As of November 2024, prices for Orlando to Chicago Midway Airport flights are approximately 93% more expensive when compared to flights at the same time last year.

Cheap Orlando to Chicago Midway Airport flight deals and tips

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

Best Price Found

$56

Fastest flight time

2h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Orlando in the past 72 hours is $56. The best round-trip flight deal from Orlando to Chicago Midway Airport found on momondo in the last 72 hours is $106.
The fastest flight from Orlando to Chicago Midway Airport takes 2h 50m
Direct flights go from Orlando to Chicago Midway Airport every day.

  • How far is Orlando to Chicago Midway by plane?

    The distance between Orlando and Chicago Midway is about 982.0 mi. Typically, this will take 2h 50m by plane in normal conditions.

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

    Prices for flights from Orlando to Chicago Midway Airport were last updated today.

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

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

    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 to Chicago Midway Airport.

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

    The required travel and health documents for your Chicago Midway 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 Midway 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 Midway Airport?

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


Best airlines flying from Orlando to Chicago Midway Airport

Compare and see reviews for airlines that fly from Orlando to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $74Free CancellationRating
6.1
3,551 reviews
Search Frontier flights
SouthwestPriceFrom $170Free CancellationRating
8.1
5,045 reviews
Search Southwest flights
DeltaPriceFrom $227Free CancellationRating
8.0
8,788 reviews
Search Delta flights
  • Southwest Flights From Orlando to Chicago Midway Airport

    Southwest operates around 53 flights from Orlando to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $288, but momondo users have found Southwest deals from Orlando to Chicago Midway Airport from as low as $170 round-trip. Southwest has been scored 8.1/10 in 5,045 reviews.

  • Frontier Flights From Orlando to Chicago Midway Airport

    Another popular option for Orlando to Chicago Midway Airport flights is Frontier (6.1/10, 3,551 ratings). Frontier flies from Orlando to Chicago Midway Airport around 1 time per week, with deals starting from $74 round-trip and rising to an average price of around $154.


Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Orlando.

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

Flights from Orlando to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Orlando to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are not ready to book a flight from Orlando to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.


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