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Cheap flights from Orlando Airport to Chicago from $46

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 1/16. 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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Find the cheapest flights from Orlando Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
5:49 pm - 7:52 pm
MCO
-
MDW
3h 03mnonstop
Frontier Logo
1:00 pm - 4:49 pm
MDW
-
MCO
2h 49mnonstop
$77Frontier
Fri, Jan 30 - Mon, Feb 2
Frontier Logo
12:39 pm - 10:19 pm
MCO
-
MDW
10h 40m1 stop
Frontier Logo
6:01 pm - 9:49 pm
MDW
-
MCO
2h 48mnonstop
$78Frontier
Thu, Jan 15 - Sun, Jan 18
Frontier Logo
8:30 am - 10:32 am
MCO
-
MDW
3h 02mnonstop
Frontier Logo
9:15 am - 11:42 pm
MDW
-
MCO
13h 27m1 stop
$79Frontier
Thu, Jan 15 - Mon, Jan 19
Frontier Logo
12:39 pm - 10:19 pm
MCO
-
MDW
10h 40m1 stop
Frontier Logo
6:01 pm - 9:49 pm
MDW
-
MCO
2h 48mnonstop
$80Frontier
Thu, Jan 15 - Sun, Jan 18
Frontier Logo
5:20 am - 11:31 am
MCO
-
MDW
7h 11m1 stop
Frontier Logo
4:21 pm - 8:08 pm
MDW
-
MCO
2h 47mnonstop
$83Frontier
Thu, Jan 8 - Sun, Jan 11
Frontier Logo
5:20 am - 11:31 am
MCO
-
MDW
7h 11m1 stop
Frontier Logo
4:21 pm - 8:08 pm
MDW
-
MCO
2h 47mnonstop
$84Frontier
Thu, Jan 8 - Sun, Jan 11
Frontier Logo
5:49 pm - 7:52 pm
MCO
-
MDW
3h 03mnonstop
Frontier Logo
5:01 pm - 12:31 am
MDW
-
MCO
6h 30m1 stop
$93Frontier
Fri, Jan 30 - Mon, Feb 2
Frontier Logo
9:03 pm - 10:59 pm
MCO
-
MDW
2h 56mnonstop
Frontier Logo
6:10 am - 5:39 pm
MDW
-
MCO
10h 29m1 stop
$94Frontier
Sun, Jan 11 - Wed, Jan 14
Frontier Logo
12:46 pm - 10:19 pm
MCO
-
MDW
10h 33m1 stop
Frontier Logo
9:38 am - 9:39 pm
MDW
-
MCO
11h 01m1 stop
$98Frontier
Thu, Jan 22 - Sat, Jan 24
Frontier Logo
5:20 am - 11:31 am
MCO
-
MDW
7h 11m1 stop
Frontier Logo
9:15 am - 11:44 pm
MDW
-
MCO
13h 29m1 stop
$99Frontier
Thu, Jan 8 - Sun, Jan 11

Southwest flights from Orlando Airport to Chicago Midway Airport

Our best Southwest deals on Orlando Airport to Chicago Midway Airport flight tickets
Southwest
Dec 25
MCO12:40 pmOrlando
2h 50m
MDW2:30 pmChicago Midway
Dec 31
MDW5:05 amChicago Midway
2h 35m
MCO8:40 amOrlando
$157
Find similar
Southwest
Dec 25
MCO2:45 pmOrlando
2h 50m
MDW4:35 pmChicago Midway
Dec 31
MDW2:25 pmChicago Midway
3h 50m
1 stop
MCO7:15 pmOrlando
$163
Find similar
Southwest
Dec 25
MCO6:20 amOrlando
5h 55m
1 stop
MDW11:15 amChicago Midway
Dec 31
MDW2:25 pmChicago Midway
3h 50m
1 stop
MCO7:15 pmOrlando
$172
Find similar

Frontier flights from Orlando Airport to Chicago Midway Airport

Our best Frontier deals on Orlando Airport 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
$77
Find similar
Frontier
Jan 15
MCO12:39 pmOrlando
10h 40m
1 stop
MDW10:19 pmChicago Midway
Jan 18
MDW6:01 pmChicago Midway
2h 48m
MCO9:49 pmOrlando
$78
Find similar
Frontier
Jan 15
MCO8:30 amOrlando
3h 02m
MDW10:32 amChicago Midway
Jan 19
MDW9:15 amChicago Midway
13h 27m
1 stop
MCO11:42 pmOrlando
$79
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Orlando Airport 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 December 11, 2025.
Use the filters below to find and compare flights from Orlando Airport 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

$77

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/15

12:39 pm-10:19 pm

1 stop10h 40m

Chicago Midway

Sun 1/18

6:01 pm-9:49 pm

Nonstop2h 48m

$78

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/15

8:30 am-10:32 am

Nonstop3h 02m

Chicago Midway

Mon 1/19

9:15 am-11:42 pm

1 stop13h 27m

$79

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/15

12:39 pm-10:19 pm

1 stop10h 40m

Chicago Midway

Sun 1/18

6:01 pm-9:49 pm

Nonstop2h 48m

$80

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/8

5:20 am-11:31 am

1 stop7h 11m

Chicago Midway

Sun 1/11

4:21 pm-8:08 pm

Nonstop2h 47m

$83

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/8

5:20 am-11:31 am

1 stop7h 11m

Chicago Midway

Sun 1/11

4:21 pm-8:08 pm

Nonstop2h 47m

$84

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 1/30

5:49 pm-7:52 pm

Nonstop3h 03m

Chicago Midway

Mon 2/2

5:01 pm-12:31 am

1 stop6h 30m

$93

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sun 1/11

9:03 pm-10:59 pm

Nonstop2h 56m

Chicago Midway

Wed 1/14

6:10 am-5:39 pm

1 stop10h 29m

$94

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/22

12:46 pm-10:19 pm

1 stop10h 33m

Chicago Midway

Sat 1/24

9:38 am-9:39 pm

1 stop11h 01m

$98

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/8

5:20 am-11:31 am

1 stop7h 11m

Chicago Midway

Sun 1/11

9:15 am-11:44 pm

1 stop13h 29m

$99

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 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 February is, on average, the cheapest month to fly to Chicago Midway Airport from Orlando Airport, with most prices found around $101. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Orlando Airport during the month January is also very affordable. Most momondo users find prices during this month for around $156.

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 Airport. 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 Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $285.

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

Flying to Chicago Midway Airport from Orlando Airport at noon is the least expensive time of day to depart. momondo users have found prices as low as $170 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $234. 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 Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $197 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 Airport 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.

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

As of December 2025, prices for Orlando Airport to Chicago Midway Airport flights are approximately 124% more expensive when compared to flights at the same time last year.

When to book flights from Orlando Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Orlando Airport 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 Airport to Chicago Midway Airport (MCO to MDW) flight deals and tips

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

Best Price Found

$107

Fastest flight time

2h 45m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Orlando Airport in the past 72 hours is $107. The best round-trip flight deal from Orlando Airport to Chicago Midway Airport found on momondo in the last 72 hours is $116.
The fastest flight from Orlando Airport to Chicago Midway Airport takes 2h 45m
Direct flights go from Orlando Airport 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 990.5 mi. 2h 45m is a normal flight duration for this route.

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

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

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

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

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

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

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

Best airlines flying from Orlando Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from Orlando Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $67Free CancellationRating
5.8
3,084 reviews
Search Frontier flights
DeltaPriceFrom $114Free CancellationRating
7.9
8,007 reviews
Search Delta flights
SouthwestPriceFrom $159Free CancellationRating
7.9
4,253 reviews
Search Southwest flights

  • Southwest Flights From Orlando Airport to Chicago Midway Airport

    The lowest priced Southwest flight from Orlando Airport to Chicago Midway Airport from the last 72 hours was $159. Generally, Southwest has 25 flights on this route every week with an average price of $305. Southwest is rated 7.9/10 by our users.

  • Frontier Flights From Orlando Airport to Chicago Midway Airport

    Frontier (5.8/10 from 3,084 reviews) operates around 2 flights from Orlando Airport to Chicago Midway Airport in any given week. The average Frontier airfare for this route is around $158, with deals from around $67 rare but found on momondo. Referenced prices are for round-trip Orlando Airport to Chicago Midway Airport flight searches in the last 72 hours.

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?

It is quick and easy to find Orlando to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

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

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

Once you have performed a search for Orlando to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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.

An easier way to manage your Chicago Midway Airport trip

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