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Cheap flights from Orlando to Chicago 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 Orlando to Chicago departing on 12/17. 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.
4:46 pm - 6:50 pmMCO-ORD
3h 04mnonstop
11:24 am - 3:18 pmORD-MCO
2h 54mnonstop
Thu, Dec 12 - Tue, Dec 17
4:46 pm - 6:50 pmMCO-ORD
3h 04mnonstop
11:24 am - 3:18 pmORD-MCO
2h 54mnonstop
Thu, Dec 12 - Tue, Dec 17
7:30 am - 9:54 amMCO-ORD
3h 24mnonstop
11:24 am - 3:18 pmORD-MCO
2h 54mnonstop
$89Frontier
Find Deal
Fri, Dec 13 - Tue, Dec 17
8:10 am - 10:28 amMCO-ORD
3h 18mnonstop
10:15 pm - 7:46 amORD-MCO
8h 31m1 stop
$93Frontier
Find Deal
Tue, Dec 17 - Thu, Jan 2
8:10 am - 10:28 amMCO-ORD
3h 18mnonstop
5:38 pm - 11:43 pmORD-MCO
5h 05m1 stop
$97Frontier
Find Deal
Tue, Dec 17 - Tue, Dec 17
9:24 am - 11:32 amMCO-ORD
3h 08mnonstop
12:37 pm - 4:24 pmORD-MCO
2h 47mnonstop
$114Spirit Airlines
Find Deal
Fri, Jan 17 - Mon, Jan 20
7:50 pm - 9:53 pmMCO-ORD
3h 03mnonstop
12:37 pm - 4:24 pmORD-MCO
2h 47mnonstop
$115Spirit Airlines
Find Deal
Wed, Jan 8 - Mon, Jan 13
1:05 pm - 3:00 pmMCO-MDW
2h 55mnonstop
7:05 pm - 10:45 pmMDW-MCO
2h 40mnonstop
$170Southwest
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Thu, Jan 9 - Sun, Jan 12
1:05 pm - 3:00 pmMCO-MDW
2h 55mnonstop
6:10 pm - 9:50 pmMDW-MCO
2h 40mnonstop
$188Southwest
Find Deal
Wed, Jan 8 - Wed, Jan 8
7:12 am - 9:30 amMCO-ORD
3h 18mnonstop
12:08 pm - 3:51 pmORD-MCO
2h 43mnonstop
$204American Airlines
Find Deal
Tue, Dec 17 - Tue, Dec 17
9:00 pm - 10:59 pmMCO-ORD
2h 59mnonstop
$37Spirit Airlines
Find Deal
Tue, Dec 17
4:00 pm - 5:54 pmMCO-MDW
2h 54mnonstop
$37Frontier
Find Deal
Tue, Dec 17
8:10 am - 10:28 amMCO-ORD
3h 18mnonstop
$38Frontier
Find Deal
Tue, Dec 17
6:54 pm - 8:58 pmMCO-ORD
3h 04mnonstop
$58Spirit Airlines
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Thu, Dec 5
6:18 pm - 8:25 pmMCO-ORD
3h 07mnonstop
$79United Airlines
Find Deal
Sat, Feb 8
11:01 am - 1:14 pmMCO-ORD
3h 13mnonstop
$85United Airlines
Find Deal
Fri, Feb 28
7:00 am - 9:05 amMCO-ORD
3h 05mnonstop
$99American Airlines
Find Deal
Sat, Feb 1
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
$114Southwest
Find Deal
Wed, Feb 19
3:57 pm - 6:07 pmMCO-ORD
3h 10mnonstop
$125American Airlines
Find Deal
Fri, Dec 13
7:10 am - 9:05 amMCO-MDW
2h 55mnonstop
$125Southwest
Find Deal
Thu, Dec 12
6:34 pm - 11:36 pmMCO-ORD
6h 02m1 stop
7:45 pm - 11:50 pmORD-MCO
3h 05mnonstop
Mon, Dec 2 - Thu, Dec 5
6:34 pm - 11:36 pmMCO-ORD
6h 02m1 stop
7:15 am - 6:55 pmORD-MCO
10h 40m1 stop
Mon, Dec 2 - Sat, Dec 7
6:34 pm - 11:36 pmMCO-ORD
6h 02m1 stop
5:25 am - 12:51 pmORD-MCO
6h 26m1 stop
Mon, Dec 2 - Thu, Dec 5
6:34 pm - 11:08 pmMCO-MDW
5h 34m1 stop
11:33 am - 3:25 pmMDW-MCO
2h 52mnonstop
$246Frontier
Find Deal
Mon, Dec 2 - Mon, Dec 9
6:34 pm - 11:36 pmMCO-ORD
6h 02m1 stop
10:59 am - 2:54 pmORD-MCO
2h 55mnonstop
$252Frontier
Find Deal
Mon, Dec 2 - Mon, Dec 9
8:50 am - 10:56 amMCO-ORD
3h 06mnonstop
7:45 pm - 11:50 pmORD-MCO
3h 05mnonstop
$286Spirit Airlines
Find Deal
Sat, Nov 30 - Thu, Dec 5
8:50 am - 10:56 amMCO-ORD
3h 06mnonstop
9:32 pm - 8:51 amORD-MCO
10h 19m1 stop
$289Spirit Airlines
Find Deal
Sat, Nov 30 - Mon, Dec 9
10:30 am - 12:33 pmMCO-ORD
3h 03mnonstop
2:40 pm - 3:12 pmORD-MCO
23h 32m2 stops
$408United Airlines
Find Deal
Thu, Nov 28 - Thu, Nov 28
8:05 pm - 9:55 pmMCO-MDW
2h 50mnonstop
7:15 pm - 10:55 pmMDW-MCO
2h 40mnonstop
$559Southwest
Find Deal
Mon, Dec 2 - Tue, Dec 3
6:35 am - 8:30 amMCO-MDW
2h 55mnonstop
7:15 pm - 10:55 pmMDW-MCO
2h 40mnonstop
$599Southwest
Find Deal
Sat, Nov 30 - Tue, Dec 3
4:46 pm - 6:50 pmMCO-ORD
3h 04mnonstop
11:24 am - 3:18 pmORD-MCO
2h 54mnonstop
Thu, Dec 12 - Tue, Dec 17
6:05 am - 8:24 amMCO-ORD
3h 19mnonstop
11:24 am - 3:18 pmORD-MCO
2h 54mnonstop
$88Frontier
Find Deal
Thu, Dec 12 - Tue, Dec 17
9:24 am - 11:32 amMCO-ORD
3h 08mnonstop
12:37 pm - 4:24 pmORD-MCO
2h 47mnonstop
$114Spirit Airlines
Find Deal
Fri, Jan 17 - Mon, Jan 20
7:50 pm - 9:53 pmMCO-ORD
3h 03mnonstop
12:37 pm - 4:24 pmORD-MCO
2h 47mnonstop
$115Spirit Airlines
Find Deal
Wed, Jan 8 - Mon, Jan 13
7:50 pm - 9:45 pmMCO-MDW
2h 55mnonstop
7:05 pm - 10:45 pmMDW-MCO
2h 40mnonstop
$158Southwest
Find Deal
Tue, Feb 4 - Tue, Feb 18
7:50 pm - 9:45 pmMCO-MDW
2h 55mnonstop
10:25 am - 2:05 pmMDW-MCO
2h 40mnonstop
$164Southwest
Find Deal
Thu, Jan 30 - Tue, Feb 4
7:00 am - 9:05 amMCO-ORD
3h 05mnonstop
6:45 pm - 10:35 pmORD-MCO
2h 50mnonstop
$177American Airlines
Find Deal
Tue, Jan 21 - Sat, Jan 25
9:45 am - 11:52 amMCO-ORD
3h 07mnonstop
6:08 pm - 10:00 pmORD-MCO
2h 52mnonstop
$302United Airlines
Find Deal
Tue, Jan 7 - Tue, Jan 7
6:05 pm - 8:16 pmMCO-ORD
3h 11mnonstop
7:58 pm - 11:50 pmORD-MCO
2h 52mnonstop
$334United Airlines
Find Deal
Wed, Mar 5 - Mon, Mar 10
6:45 am - 8:52 amMCO-ORD
3h 07mnonstop
7:05 am - 10:49 amORD-MCO
2h 44mnonstop
$377American Airlines
Find Deal
Fri, Dec 20 - Wed, Jan 1

Spirit Airlines flights from Orlando to Chicago

Our best Spirit Airlines deals on Orlando to Chicago flight tickets
Spirit Airlines
Dec 5
MCO4:46 pmOrlando
3h 04m
ORD6:50 pmChicago O'Hare Intl
Dec 9
ORD9:32 pmChicago O'Hare Intl
10h 19m
1 stop
MCO8:51 amOrlando
Spirit Airlines
Jan 17
MCO9:24 amOrlando
3h 08m
ORD11:32 amChicago O'Hare Intl
Jan 20
ORD12:37 pmChicago O'Hare Intl
2h 47m
MCO4:24 pmOrlando
Spirit Airlines
Jan 8
MCO7:50 pmOrlando
3h 03m
ORD9:53 pmChicago O'Hare Intl
Jan 13
ORD12:37 pmChicago O'Hare Intl
2h 47m
MCO4:24 pmOrlando

Frontier flights from Orlando to Chicago

Our best Frontier deals on Orlando to Chicago flight tickets
Frontier
Dec 13
MCO7:30 amOrlando
3h 24m
ORD9:54 amChicago O'Hare Intl
Dec 17
ORD11:24 amChicago O'Hare Intl
2h 54m
MCO3:18 pmOrlando
Frontier
Dec 5
MCO6:05 amOrlando
3h 19m
ORD8:24 amChicago O'Hare Intl
Dec 8
ORD9:35 amChicago O'Hare Intl
2h 55m
MCO1:30 pmOrlando
Frontier
Dec 17
MCO8:10 amOrlando
3h 18m
ORD10:28 amChicago O'Hare Intl
Jan 2
ORD10:15 pmChicago O'Hare Intl
8h 31m
1 stop
MCO7:46 amOrlando

See travel insights to Chicago from

How to get the cheapest flight ticket from Orlando 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 February is, on average, the cheapest month to fly to Chicago from Orlando, with most prices found around $118. If you’re not able to fly to Chicago in February, then April is your next best option. Flight prices from Orlando to Chicago during April average around $123.

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 $181. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Orlando to Chicago for around $256.

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 to Chicago during this time can be as low as $124. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $220.

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?

The best time to book a flight to Chicago from Orlando is 29 days out, which is when prices tend to be around $169. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $94.

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.

Can stopping save me money on Orlando to Chicago flights?

You could potentially save up to 40% on your flight if you consider stops on a Orlando to Chicago flight.

How have Orlando to Chicago flight prices changed over time?

As of November 2024, prices for Orlando to Chicago flights are approximately 12% cheaper when compared to flights at the same time last year.

Cheap Orlando to Chicago flight deals and tips

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

Best Price Found

$37

Fastest flight time

2h 48m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Orlando in the past 72 hours is $37. The best round-trip flight deal from Orlando to Chicago found on momondo in the last 72 hours is $86.
The fastest flight from Orlando to Chicago takes 2h 48m
Direct flights go from Orlando to Chicago every day.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

  • Is flying the fastest way to get from Orlando to Chicago?

    To save time, the fastest way to travel is by flight from Orlando to Chicago on Allegiant Air. Expect the length of time you’ll spend onboard Allegiant Air to be about 2h 48m compared to taking a train from Orlando to Chicago or a bus from Orlando to Chicago which have been found to be slower alternatives.

  • Is flying the cheapest way to get from Orlando to Chicago?

    A flight from Orlando to Chicago from $86 can save you up to 87% on the cost of your trip compared to booking a train from Orlando to Chicago or a bus from Orlando to Chicago.

  • How far is Orlando to Chicago by plane?

    Chicago is 985.3 mi away from Orlando. 2h 48m is a normal flight duration for this route.

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

    Prices for flights from Orlando to Chicago refresh daily.

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

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

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

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

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


Best airlines flying from Orlando to Chicago

Compare and see reviews for airlines that fly from Orlando to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $57Free CancellationRating
6.1
3,523 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $57Free CancellationRating
6.3
8,172 reviews
Search Spirit Airlines flights
Allegiant AirPriceFrom $109Free CancellationRating
7.3
843 reviews
Search Allegiant Air flights
United AirlinesPriceFrom $152Free CancellationRating
7.4
9,146 reviews
Search United Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $178Free CancellationRating
8.1
4,979 reviews
Search Southwest flights
DeltaPriceFrom $227Free CancellationRating
8.0
8,730 reviews
Search Delta flights
  • Southwest Flights From Orlando to Chicago

    Southwest is one of the most popular airlines flying from Orlando to Chicago, operating 30 flights/week on average for this route. A good Southwest flight deal for Orlando to Chicago starts from $178 round-trip, up to an average price of $367. Our users have rated Southwest at 8.1/10.

  • United Airlines Flights From Orlando to Chicago

    $152 is the best United Airlines flight deal from Orlando to Chicago found on momondo over the last 72 hours. The average United Airlines ticket price found was closer to $318, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 9,146 user reviews) flies into Chicago from Orlando 22 times in an average week so prices can vary.


Why use momondo?

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

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

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 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 Chicago from Orlando.

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.


Choose the best way to get from Orlando to Chicago

Buses

50h 55m
$340 one-way$680 round-trip
Nonstop · from $680

Distance to downtown

P324.7 mi

Find Buses

Orlando to Chicago Buses

Trains

38h 38m
$118 one-way$236 round-trip
Nonstop · from $236

Distance to downtown

ZUN0.7 mi

Flights

2h 50m
$37 one-way$86 round-trip
Nonstop · from $861 stop · from $93

Distance to downtown

ORD15.9 mi

An easier way to manage your Chicago trip

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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