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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 5/10. 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 to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Orlando to Chicago.
Allegiant Air Logo
6:00 am - 7:46 amSFB-RFD
2h 46mnonstop
Allegiant Air Logo
5:41 pm - 9:11 pmRFD-SFB
2h 30mnonstop
$76Allegiant Air
Find Deal
Wed, May 14 - Fri, May 16
Frontier Logo
9:23 pm - 11:32 pmMCO-ORD
3h 09mnonstop
Frontier Logo
4:15 pm - 8:18 pmORD-MCO
3h 03mnonstop
$78Frontier
Find Deal
Sat, May 10 - Sat, May 17
Frontier Logo
9:57 pm - 12:04 amMCO-ORD
3h 07mnonstop
Frontier Logo
5:14 pm - 9:11 pmORD-MCO
2h 57mnonstop
$86Frontier
Find Deal
Sat, May 24 - Sun, May 25
Spirit Airlines Logo
5:55 pm - 8:03 pmMCO-ORD
3h 08mnonstop
Spirit Airlines Logo
7:47 am - 11:26 amORD-MCO
2h 39mnonstop
$96Spirit Airlines
Find Deal
Sat, May 10 - Wed, May 14
Spirit Airlines Logo
9:25 pm - 11:29 pmMCO-ORD
3h 04mnonstop
Spirit Airlines Logo
7:47 am - 11:26 amORD-MCO
2h 39mnonstop
$97Spirit Airlines
Find Deal
Sat, May 10 - Wed, May 14
Southwest Logo
6:45 pm - 8:35 pmMCO-MDW
2h 50mnonstop
Southwest Logo
8:25 am - 12:05 pmMDW-MCO
2h 40mnonstop
$179Southwest
Find Deal
Sat, May 24 - Sun, May 25
Southwest Logo
2:45 pm - 4:35 pmMCO-MDW
2h 50mnonstop
Southwest Logo
6:35 pm - 10:10 pmMDW-MCO
2h 35mnonstop
$208Southwest
Find Deal
Sat, May 24 - Mon, May 26
American Airlines Logo
8:41 am - 10:43 amMCO-ORD
3h 02mnonstop
American Airlines Logo
6:00 am - 1:12 pmORD-MCO
6h 12m1 stop
$218American Airlines
Find Deal
Tue, Jul 1 - Sun, Jul 6
American Airlines Logo
6:52 am - 8:59 amMCO-ORD
3h 07mnonstop
American Airlines Logo
6:38 pm - 10:28 pmORD-MCO
2h 50mnonstop
$226American Airlines
Find Deal
Wed, May 21 - Mon, May 26
United Airlines Logo
7:15 am - 9:25 amMCO-ORD
3h 10mnonstop
United Airlines Logo
1:58 pm - 5:57 pmORD-MCO
2h 59mnonstop
$227United Airlines
Find Deal
Wed, May 21 - Mon, May 26

Spirit Airlines flights from Orlando to Chicago

Our best Spirit Airlines deals on Orlando to Chicago flight tickets
Spirit Airlines
May 10
MCO5:55 pmOrlando
3h 08m
ORD8:03 pmChicago O'Hare Intl
May 14
ORD7:47 amChicago O'Hare Intl
2h 39m
MCO11:26 amOrlando
Spirit Airlines
May 10
MCO9:25 pmOrlando
3h 04m
ORD11:29 pmChicago O'Hare Intl
May 14
ORD7:47 amChicago O'Hare Intl
2h 39m
MCO11:26 amOrlando
Spirit Airlines
May 7
MCO10:17 pmOrlando
11h 38m
1 stop
ORD8:55 amChicago O'Hare Intl
May 10
ORD4:35 pmChicago O'Hare Intl
2h 45m
MCO8:20 pmOrlando

Frontier flights from Orlando to Chicago

Our best Frontier deals on Orlando to Chicago flight tickets
Frontier
May 10
MCO9:23 pmOrlando
3h 09m
ORD11:32 pmChicago O'Hare Intl
May 17
ORD4:15 pmChicago O'Hare Intl
3h 03m
MCO8:18 pmOrlando
Frontier
May 24
MCO9:57 pmOrlando
3h 07m
ORD12:04 amChicago O'Hare Intl
May 25
ORD5:14 pmChicago O'Hare Intl
2h 57m
MCO9:11 pmOrlando
Frontier
May 23
MCO10:17 pmOrlando
3h 03m
ORD12:20 amChicago O'Hare Intl
May 25
ORD5:14 pmChicago O'Hare Intl
2h 57m
MCO9:11 pmOrlando

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

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Orlando, with most prices found around $133. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from Orlando to Chicago during May average around $143.

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 $235. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Orlando to Chicago for around $503.

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 $158. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $720.

What is the cheapest Orlando to Chicago flight route?

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

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

You are more likely to see cheaper flights to Chicago from Orlando when booking 13 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $220 when searching 13 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Orlando for as low as $156 on momondo.

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.

How have Orlando to Chicago flight prices changed over time?

As of April 2025, prices for Orlando to Chicago flights are approximately 16% more expensive when compared to flights at the same time last year.

When to book flights from Orlando to Chicago

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

Cheap Orlando to Chicago (ORL to CHI) 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 39m

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 $76.
The fastest flight from Orlando to Chicago takes 2h 39m
Direct flights go from Orlando to Chicago every day.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Greater Rockford (RFD), Chicago Midway (MDW)

  • 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 39m 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 $76 can save you up to 90% 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 39m 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 $64Free CancellationRating
5.9
3,283 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $70Free CancellationRating
6.3
7,942 reviews
Search Spirit Airlines flights
Allegiant AirPriceFrom $100Free CancellationRating
7.3
734 reviews
Search Allegiant Air flights
United AirlinesPriceFrom $157Free CancellationRating
7.4
8,685 reviews
Search United Airlines flights
American AirlinesPriceFrom $161Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $184Free CancellationRating
8.0
4,286 reviews
Search Southwest flights
DeltaPriceFrom $227Free CancellationRating
8.0
7,920 reviews
Search Delta flights
  • Southwest Flights From Orlando to Chicago

    Southwest is one of the most popular airlines flying from Orlando to Chicago, operating 55 flights/week on average for this route. A good Southwest flight deal for Orlando to Chicago starts from $184 round-trip, up to an average price of $388. Our users have rated Southwest at 8.0/10.

  • United Airlines Flights From Orlando to Chicago

    $157 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 $329, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 8,685 user reviews) flies into Chicago from Orlando 40 times in an average week so prices can vary.


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
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
Saint John

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
$375 one-way$770 round-trip
Nonstop · from $770

Distance to downtown

P324.7 mi

Find Buses

Orlando to Chicago Buses

Trains

38h 38m
$127 one-way$254 round-trip
Nonstop · from $254

Distance to downtown

ZUN0.7 mi

Flights

2h 39m
$37 one-way$76 round-trip
Nonstop · from $761 stop · from $99

Distance to downtown

ORD15.9 mi
RFD78.5 mi

An easier way to manage your Chicago trip

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1 adult
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Wed 4/30
Wed 5/7

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