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Cheap flights from Orlando to Chicago from £69

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 7/5. 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 return flights

KAYAK's recommended return flight deals from the most popular airlines that fly from Orlando to Chicago.
21:23 - 23:32MCO-ORD
3h 09mdirect
16:15 - 20:18ORD-MCO
3h 03mdirect
£77Frontier
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Fri, 9 May - Sat, 10 May
17:55 - 20:03MCO-ORD
3h 08mdirect
13:59 - 21:00ORD-MCO
6h 01m1 stop
£112Spirit Airlines
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Fri, 9 May - Sat, 10 May
11:00 - 13:05MCO-ORD
3h 05mdirect
16:00 - 19:50ORD-MCO
2h 50mdirect
£144Southwest
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Wed, 21 May - Sat, 24 May
11:00 - 13:05MCO-ORD
3h 05mdirect
16:00 - 19:50ORD-MCO
2h 50mdirect
£146Southwest
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Tue, 27 May - Sat, 31 May
05:30 - 08:40MCO-ORD
4h 10m1 stop
09:30 - 16:30ORD-MCO
6h 00m1 stop
£155Delta
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Tue, 24 Jun - Tue, 8 Jul
12:16 - 14:23MCO-ORD
3h 07mdirect
07:10 - 11:04ORD-MCO
2h 54mdirect
£168United Airlines
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Sat, 24 May - Mon, 26 May
05:30 - 10:03MCO-ORD
5h 33m1 stop
17:15 - 23:13ORD-MCO
4h 58m1 stop
£175Delta
Find Deal
Tue, 20 May - Fri, 30 May
20:20 - 18:39MCO-ORD
23h 19m1 stop
19:05 - 12:56ORD-MCO
16h 51m1 stop
£205Sun Country Air
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Thu, 24 Apr - Mon, 28 Apr
20:20 - 18:39MCO-ORD
23h 19m1 stop
08:15 - 18:56ORD-MCO
9h 41m1 stop
£212Sun Country Air
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Thu, 24 Apr - Sun, 27 Apr
09:32 - 11:39MCO-ORD
3h 07mdirect
17:50 - 21:46ORD-MCO
2h 56mdirect
£222United Airlines
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Sat, 12 Jul - Mon, 14 Jul

Southwest flights from Orlando to Chicago

Our best Southwest deals on Orlando to Chicago flight tickets
Southwest
21 May
MCO11:00Orlando
3h 05m
ORD13:05Chicago O'Hare Intl
24 May
ORD16:00Chicago O'Hare Intl
2h 50m
MCO19:50Orlando
Southwest
27 May
MCO11:00Orlando
3h 05m
ORD13:05Chicago O'Hare Intl
31 May
ORD16:00Chicago O'Hare Intl
2h 50m
MCO19:50Orlando
Southwest
9 Jul
MCO06:50Orlando
9h 10m
2 stops
ORD15:00Chicago O'Hare Intl
15 Jul
ORD06:00Chicago O'Hare Intl
2h 40m
MCO09:40Orlando

United Airlines flights from Orlando to Chicago

Our best United Airlines deals on Orlando to Chicago flight tickets
United Airlines
24 May
MCO12:16Orlando
3h 07m
ORD14:23Chicago O'Hare Intl
26 May
ORD07:10Chicago O'Hare Intl
2h 54m
MCO11:04Orlando
United Airlines
12 Jul
MCO09:32Orlando
3h 07m
ORD11:39Chicago O'Hare Intl
14 Jul
ORD17:50Chicago O'Hare Intl
2h 56m
MCO21:46Orlando
United Airlines
18 Jul
MCO11:00Orlando
3h 07m
ORD13:07Chicago O'Hare Intl
20 Jul
ORD07:10Chicago O'Hare Intl
2h 54m
MCO11:04Orlando

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 cheapest month to fly to Chicago from Orlando is in April. Flight prices, which tend to average around £112, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of April, then book flights to Chicago from Orlando during May instead. Flights to Chicago in May, while not as cheap as those in April, still average around £112.

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 Wednesday when prices can be found for as low as £207. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Thursday, with ticket prices averaging around £518.

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

Flying to Chicago from Orlando in the morning is the least expensive time of day to depart. momondo users have found prices as low as £271 when looking at flights departing in the morning. Flights at midday are often more expensive, with an average ticket price of £519.

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?

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 £163 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 £126 on momondo.

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

There are 2 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 March 2025, prices for Orlando to Chicago flights are approximately 3% 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

£69

Fastest flight time

3h 05m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun

Airports in Chicago

1 airport
The best one-way flight to Chicago from Orlando in the past 72 hours is £69. The best return flight deal from Orlando to Chicago found on momondo in the last 72 hours is £77.
The fastest flight from Orlando to Chicago takes 3h 05m
Direct flights go from Orlando to Chicago on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines, Southwest and Frontier.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

  • How far is Orlando to Chicago by plane?

    The distance between Orlando and Chicago is about 985.3 mi. Typically, this will take 3h 05m by plane in normal conditions.

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

    Prices for flights from Orlando to Chicago refresh daily.

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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 travel and health documents you'll need for your trip to Chicago 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. 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 to Chicago?


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?

Yes. momondo enables you to select and highlight flights to Chicago from Orlando with this policy.

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

momondo provides multiple filters to help you find the best flight to Chicago from Orlando. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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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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