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Cheap flights from Orlando 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 to Chicago departing on 12/19. 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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0 bags

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Cheap round-trip flights

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Frontier Logo
5:49 pm - 7:52 pmMCO-MDW
3h 03mnonstop
Frontier Logo
1:00 pm - 4:49 pmMDW-MCO
2h 49mnonstop
$75Frontier
Find Deal
Fri, Jan 30 - Mon, Feb 2
Frontier Logo
7:58 pm - 9:58 pmMCO-MDW
3h 00mnonstop
Frontier Logo
3:10 pm - 6:58 pmMDW-MCO
2h 48mnonstop
$77Frontier
Find Deal
Wed, Dec 24 - Thu, Jan 1
Frontier Logo
7:58 pm - 9:58 pmMCO-MDW
3h 00mnonstop
Frontier Logo
3:10 pm - 6:58 pmMDW-MCO
2h 48mnonstop
$82Frontier
Find Deal
Thu, Dec 25 - Wed, Dec 31
Frontier Logo
8:40 pm - 10:39 pmMCO-MDW
2h 59mnonstop
Frontier Logo
6:37 pm - 10:23 pmMDW-MCO
2h 46mnonstop
$83Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
12:57 pm - 10:17 pmMCO-MDW
10h 20m1 stop
Frontier Logo
4:21 pm - 8:08 pmMDW-MCO
2h 47mnonstop
$84Frontier
Find Deal
Thu, Jan 8 - Fri, Jan 9
Frontier Logo
8:40 pm - 10:39 pmMCO-MDW
2h 59mnonstop
Frontier Logo
6:37 pm - 10:23 pmMDW-MCO
2h 46mnonstop
$87Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
12:15 pm - 10:12 pmMCO-MDW
10h 57m1 stop
Frontier Logo
3:10 pm - 6:58 pmMDW-MCO
2h 48mnonstop
$88Frontier
Find Deal
Mon, Dec 22 - Wed, Dec 31
Frontier Logo
5:30 am - 2:04 pmMCO-MDW
9h 34m1 stop
Frontier Logo
6:37 pm - 10:23 pmMDW-MCO
2h 46mnonstop
$89Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
7:58 pm - 9:58 pmMCO-MDW
3h 00mnonstop
Frontier Logo
3:10 pm - 6:58 pmMDW-MCO
2h 48mnonstop
$90Frontier
Find Deal
Thu, Dec 25 - Thu, Jan 1
Frontier Logo
2:34 pm - 4:30 pmMCO-MDW
2h 56mnonstop
Frontier Logo
4:46 pm - 8:34 pmMDW-MCO
2h 48mnonstop
$91Frontier
Find Deal
Thu, Nov 27 - Fri, Nov 28

Frontier flights from Orlando to Chicago Midway Airport

Our best Frontier deals on Orlando to Chicago Midway Airport flight tickets
Frontier
Jan 30
MCO5:49 pmOrlando
3h 03m
MDW7:52 pmChicago Midway
Feb 2
MDW1:00 pmChicago Midway
2h 49m
MCO4:49 pmOrlando
$75
Find similar
Frontier
Nov 24
MCO2:56 pmOrlando
2h 56m
MDW4:52 pmChicago Midway
Nov 27
MDW5:30 pmChicago Midway
2h 48m
MCO9:18 pmOrlando
$76
Find similar
Frontier
Nov 22
MCO3:10 pmOrlando
2h 57m
MDW5:07 pmChicago Midway
Nov 27
MDW5:30 pmChicago Midway
2h 48m
MCO9:18 pmOrlando
$77
Find similar

Southwest flights from Orlando to Chicago Midway Airport

Our best Southwest deals on Orlando to Chicago Midway Airport flight tickets
Southwest
Nov 24
MCO2:05 pmOrlando
4h 40m
1 stop
MDW5:45 pmChicago Midway
Nov 27
MDW11:50 amChicago Midway
7h 25m
1 stop
MCO8:15 pmOrlando
$157
Find similar
Southwest
Nov 24
MCO2:05 pmOrlando
4h 40m
1 stop
MDW5:45 pmChicago Midway
Nov 27
MDW9:00 amChicago Midway
4h 15m
1 stop
MCO2:15 pmOrlando
$187
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Orlando to Chicago Midway 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 November 17, 2025.
Use the filters below to find and compare flights from Orlando to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 1/30

5:49 pm-7:52 pm

Nonstop3h 03m

Chicago Midway

Mon 2/2

1:00 pm-4:49 pm

Nonstop2h 49m

$75

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 12/24

7:58 pm-9:58 pm

Nonstop3h 00m

Chicago Midway

Thu 1/1

3:10 pm-6:58 pm

Nonstop2h 48m

$77

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 12/25

7:58 pm-9:58 pm

Nonstop3h 00m

Chicago Midway

Wed 12/31

3:10 pm-6:58 pm

Nonstop2h 48m

$82

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 12/5

8:40 pm-10:39 pm

Nonstop2h 59m

Chicago Midway

Sun 12/7

6:37 pm-10:23 pm

Nonstop2h 46m

$83

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/8

12:57 pm-10:17 pm

1 stop10h 20m

Chicago Midway

Fri 1/9

4:21 pm-8:08 pm

Nonstop2h 47m

$84

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 12/5

8:40 pm-10:39 pm

Nonstop2h 59m

Chicago Midway

Sun 12/7

6:37 pm-10:23 pm

Nonstop2h 46m

$87

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 12/22

12:15 pm-10:12 pm

1 stop10h 57m

Chicago Midway

Wed 12/31

3:10 pm-6:58 pm

Nonstop2h 48m

$88

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 12/4

5:30 am-2:04 pm

1 stop9h 34m

Chicago Midway

Sun 12/7

6:37 pm-10:23 pm

Nonstop2h 46m

$89

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 12/25

7:58 pm-9:58 pm

Nonstop3h 00m

Chicago Midway

Thu 1/1

3:10 pm-6:58 pm

Nonstop2h 48m

$90

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 11/27

2:34 pm-4:30 pm

Nonstop2h 56m

Chicago Midway

Fri 11/28

4:46 pm-8:34 pm

Nonstop2h 48m

$91

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 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 to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Orlando, with most prices found around $93. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Orlando during the month February is also very affordable. Most momondo users find prices during this month for around $113.

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

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Orlando. The lowest ticket price found for a Friday departure recently was $177. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Tuesday 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 $290.

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

Flying to Chicago Midway Airport from Orlando at noon is the least expensive time of day to depart. momondo users have found prices as low as $174 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $268. 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 Midway flight route?

Fly from Orlando to Chicago Midway for the best Orlando - Chicago Midway flight prices

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

You are more likely to see cheaper flights to Chicago Midway Airport from Orlando when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $201 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Orlando for as low as $158 on momondo.

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

There is only 1 cabin class available to choose from on Orlando to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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 2025, prices for Orlando to Chicago Midway Airport flights are approximately 41% more expensive when compared to flights at the same time last year.

When to book flights from Orlando to Chicago Midway Airport

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

Cheap Orlando to Chicago Midway Airport (ORL to MDW) 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

$95

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 $95. The best round-trip flight deal from Orlando to Chicago Midway Airport found on momondo in the last 72 hours is $98.
The fastest flight from Orlando to Chicago Midway Airport takes 2h 50m
Direct flights go from Orlando to Chicago Midway Airport every day.
Search flight deals

  • 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 56m 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 $68Free CancellationRating
5.8
3,106 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $88Free CancellationRating
6.3
8,144 reviews
Search Spirit Airlines flights
DeltaPriceFrom $114Free CancellationRating
7.9
8,006 reviews
Search Delta flights
SouthwestPriceFrom $159Free CancellationRating
8.0
4,244 reviews
Search Southwest flights

  • Southwest Flights From Orlando to Chicago Midway Airport

    Southwest operates around 44 flights from Orlando to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $321, but momondo users have found Southwest deals from Orlando to Chicago Midway Airport from as low as $159 round-trip. Southwest has been scored 8.0/10 in 4,244 reviews.

  • Frontier Flights From Orlando to Chicago Midway Airport

    Another popular option for Orlando to Chicago Midway Airport flights is Frontier (5.8/10, 3,106 ratings). Frontier flies from Orlando to Chicago Midway Airport around 1 time per week, with deals starting from $68 round-trip and rising to an average price of around $165.

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
Portage
Lansing
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?

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.

An easier way to manage your Chicago Midway Airport trip

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