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Cheap flights from Orlando to Chicago from £62

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 25/6. 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 return flights

KAYAK's recommended return flight deals from the most popular airlines that fly from Orlando to Chicago.
Southwest Logo
11:00 - 13:05MCO-ORD
3h 05mdirect
Southwest Logo
11:25 - 15:05ORD-MCO
2h 40mdirect
£134Southwest
Find Deal
Wed, 21 May - Sun, 25 May
Southwest Logo
15:45 - 17:55MCO-ORD
3h 10mdirect
Southwest Logo
11:25 - 15:05ORD-MCO
2h 40mdirect
£142Southwest
Find Deal
Wed, 2 Jul - Wed, 9 Jul
Southwest Logo
11:05 - 13:05MCO-ORD
3h 00mdirect
Southwest Logo
19:15 - 23:15ORD-MCO
3h 00mdirect
£149Southwest
Find Deal
Tue, 17 Jun - Sat, 21 Jun
Delta Logo
14:00 - 18:48MCO-ORD
5h 48m1 stop
Delta Logo
10:30 - 18:54ORD-MCO
7h 24m1 stop
£150Delta
Find Deal
Sat, 24 May - Sun, 25 May
Delta Logo
17:50 - 21:24MCO-ORD
4h 34m1 stop
Delta Logo
11:19 - 19:46ORD-MCO
7h 27m1 stop
£157Delta
Find Deal
Wed, 2 Jul - Sat, 12 Jul
United Airlines Logo
09:35 - 11:41MCO-ORD
3h 06mdirect
United Airlines Logo
15:55 - 19:46ORD-MCO
2h 51mdirect
£161United Airlines
Find Deal
Wed, 27 Aug - Sun, 31 Aug
United Airlines Logo
14:30 - 16:36MCO-ORD
3h 06mdirect
United Airlines Logo
08:50 - 15:07ORD-MCO
5h 17m1 stop
£168United Airlines
Find Deal
Wed, 27 Aug - Sun, 31 Aug
JetBlue Logo
06:20 - 15:04MCO-ORD
9h 44m1 stop
JetBlue Logo
06:15 - 16:41ORD-MCO
9h 26m1 stop
£227JetBlue
Find Deal
Wed, 28 May - Fri, 30 May
Sun Country Air Logo
11:49 - 18:45MCO-ORD
7h 56m1 stop
Sun Country Air Logo
11:41 - 18:39ORD-MCO
5h 58m1 stop
£245Sun Country Air
Find Deal
Thu, 9 Oct - Mon, 13 Oct
JetBlue Logo
06:00 - 15:04MCO-ORD
10h 04m1 stop
JetBlue Logo
08:45 - 17:41ORD-MCO
7h 56m1 stop
£251JetBlue
Find Deal
Tue, 3 Jun - Thu, 5 Jun

Alaska Airlines flights from Orlando to Chicago

Our best Alaska Airlines deals on Orlando to Chicago flight tickets
Alaska Airlines
21 May
MCO07:05Orlando
17h 51m
2 stops
ORD23:56Chicago O'Hare Intl
25 May
ORD19:59Chicago O'Hare Intl
18h 31m
1 stop
MCO15:30Orlando
Alaska Airlines
20 May
MCO07:05Orlando
17h 51m
2 stops
ORD23:56Chicago O'Hare Intl
30 May
ORD17:58Chicago O'Hare Intl
12h 41m
1 stop
MCO07:39Orlando
Alaska Airlines
29 May
MCO07:05Orlando
17h 54m
1 stop
ORD23:59Chicago O'Hare Intl
3 Jun
ORD19:59Chicago O'Hare Intl
20h 01m
2 stops
MCO17:00Orlando

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
25 May
ORD11:25Chicago O'Hare Intl
2h 40m
MCO15:05Orlando
Southwest
2 Jul
MCO15:45Orlando
3h 10m
ORD17:55Chicago O'Hare Intl
9 Jul
ORD11:25Chicago O'Hare Intl
2h 40m
MCO15:05Orlando
Southwest
17 Jun
MCO11:05Orlando
3h 00m
ORD13:05Chicago O'Hare Intl
21 Jun
ORD19:15Chicago O'Hare Intl
3h 00m
MCO23:15Orlando

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 September. Flight prices, which tend to average around £100, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from Orlando during May instead. Flights to Chicago in May, while not as cheap as those in September, still average around £109.

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 £203. 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 £507.

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 £265 when looking at flights departing in the morning. Flights at midday are often more expensive, with an average ticket price of £507.

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 £166 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 £118 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 April 2025, prices for Orlando to Chicago flights are approximately 12% 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 return 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

£62

Fastest flight time

3h 00m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Orlando in the past 72 hours is £62. The best return flight deal from Orlando to Chicago found on momondo in the last 72 hours is £134.
The fastest flight from Orlando to Chicago takes 3h 00m
Direct flights go from Orlando to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

  • 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 Southwest. Expect the length of time you’ll spend onboard Southwest to be about 3h 00m 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 is currently going to be the least expensive option currently available. You can also find deals for a train from Orlando to Chicago starting at £192, or consider a bus from Orlando to Chicago starting at £581. Both of these alternative options are worth considering when looking to reach your destination.

  • How far is Orlando to Chicago by plane?

    The distance between Orlando and Chicago is about 985.3 mi. Typically, this will take 3h 00m 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.


Choose the best way to get from Orlando to Chicago

Buses

50h 55m
£291 one-way£581 return
Direct · from £581

Distance to city centre

P324.7 mi

Find Buses

Orlando to Chicago Buses

Trains

38h 38m
£93 one-way£192 return
Direct · from £192

Distance to city centre

ZUN0.7 mi

Find Trains

Orlando to Chicago Trains

Flights

3h 06m
£62 one-way£134 return
Direct · from £1341 stop · from £86

Distance to city centre

ORD15.9 mi

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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