How far in advance should I book tickets for a flight with United Airlines from Orlando Airport to Chicago?

Generally, when trying to get a below average price for your ticket, try to book around 7 days before departure. For the cheapest possible price, our data suggests booking 74 days before departure.

Is United Airlines the cheapest airline to fly with from Orlando Airport to Chicago?

With an average price of $331 return, United Airlines is not the cheapest airline to fly from Orlando Airport to Chicago with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $168 on average.

Does United Airlines fly direct to Chicago from Orlando Airport?

Yes, United Airlines does offer direct flights for the route, with around 39 flights per week.

What’s the cheapest day of the week to fly from Orlando Airport to Chicago with United Airlines?

On average, the cheapest day of the week to fly from Orlando Airport to Chicago with United Airlines is Tuesday, when prices are around $78. The most expensive day is generally Saturday, where the average price is around $133.

What’s the cheapest month to fly from Orlando Airport to Chicago with United Airlines?

The cheapest month for United Airlines flights to Chicago from Orlando Airport is generally July, where plane tickets cost $153 on average. If possible, try to avoid the most expensive months of August and October, where tickets cost $320 and $408 respectively.

$87 Cheap United Airlines Flights from Orlando Airport to Chicago

Flights Deals

Cheap United Airlines Flight Deals from Orlando Airport to Chicago

Here are some of the best deals found on KAYAK recently from United Airlines for round-trip flights from Orlando Airport to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Round-trip

One-way

Last minute

Direct

Recent round-trip United Airlines flight deals from Orlando Airport to Chicago

KAYAK's recommended round-trip United Airlines deals departing in the coming months from Orlando Airport to Chicago.

Discover the best prices for you by selecting your travel dates on KAYAK.

9:10 am - 2:33 pmMCO-ORD

6h 23m1 stop

5:50 pm - 9:46 pmORD-MCO

2h 56mnonstop

$266United Airlines

Find Deal

Sun, May 25 - Tue, May 27

7:30 am - 9:37 amMCO-ORD

3h 07mnonstop

1:58 pm - 5:57 pmORD-MCO

2h 59mnonstop

$295United Airlines

Find Deal

Fri, May 30 - Fri, May 30

7:30 am - 9:37 amMCO-ORD

3h 07mnonstop

5:50 pm - 9:46 pmORD-MCO

2h 56mnonstop

$315United Airlines

Find Deal

Sat, May 31 - Sat, May 31

8:00 am - 2:29 pmMCO-ORD

7h 29m1 stop

7:30 am - 11:42 pmORD-MCO

15h 12m2 stops

$351United Airlines

Find Deal

Sat, Aug 30 - Tue, Sep 2

4:10 pm - 6:20 pmMCO-ORD

3h 10mnonstop

5:50 pm - 9:41 pmORD-MCO

2h 51mnonstop

$357United Airlines

Find Deal

Sat, May 17 - Tue, May 20

11:55 am - 4:48 pmMCO-ORD

5h 53m1 stop

10:35 am - 12:45 amORD-MCO

13h 10m2 stops

$472United Airlines

Find Deal

Wed, Jun 11 - Mon, Jun 16

9:04 am - 2:33 pmMCO-ORD

6h 29m1 stop

8:06 pm - 10:52 amORD-MCO

13h 46m2 stops

$526United Airlines

Find Deal

Wed, Jun 11 - Wed, Jun 11

9:32 am - 11:39 amMCO-ORD

3h 07mnonstop

3:55 pm - 7:46 pmORD-MCO

2h 51mnonstop

$730United Airlines

Find Deal

Fri, Aug 15 - Tue, Aug 19

2:30 pm - 4:37 pmMCO-ORD

3h 07mnonstop

11:01 am - 2:56 pmORD-MCO

2h 55mnonstop

$743United Airlines

Find Deal

Fri, May 23 - Wed, May 28

4:11 pm - 6:25 pmMCO-ORD

3h 14mnonstop

12:50 pm - 7:51 pmORD-MCO

6h 01m1 stop

$760United Airlines

Find Deal

Fri, Aug 15 - Tue, Aug 19

Useful Info

Low season	January
High season	August
Cheapest flight	$87
Average price round-trip	$162
Good deal one-way	$443

Best time to beat the crowds but there is an average 1% increase in price.

Most popular time to fly and prices are also 3% lower on average.

Flight from Orlando to Chicago O'Hare Airport

(avg. price over the last 2 weeks)

or less

When to Book Flights with United Airlines from Orlando Airport to Chicago

Average price per month

Flight prices as travel date approaches

How far in advance should I book tickets for a flight with United Airlines from Orlando Airport to Chicago?
Generally, when trying to get a below average price for your ticket, try to book around 7 days before departure. For the cheapest possible price, our data suggests booking 74 days before departure.
Is United Airlines the cheapest airline to fly with from Orlando Airport to Chicago?
With an average price of $331 return, United Airlines is not the cheapest airline to fly from Orlando Airport to Chicago with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $168 on average.
What is the cheapest United Airlines flight from Orlando Airport to Chicago?
In the last 3 days, the lowest price for a flight with United Airlines from Orlando Airport to Chicago was $107 for a return flight and $58 for a one-way flight.
Does United Airlines fly direct to Chicago from Orlando Airport?
Yes, United Airlines does offer direct flights for the route, with around 39 flights per week.
What’s the cheapest day of the week to fly from Orlando Airport to Chicago with United Airlines?
On average, the cheapest day of the week to fly from Orlando Airport to Chicago with United Airlines is Tuesday, when prices are around $78. The most expensive day is generally Saturday, where the average price is around $133.
What’s the cheapest month to fly from Orlando Airport to Chicago with United Airlines?
The cheapest month for United Airlines flights to Chicago from Orlando Airport is generally July, where plane tickets cost $153 on average. If possible, try to avoid the most expensive months of August and October, where tickets cost $320 and $408 respectively.

7.4

GoodBased on 8,702 verified guest reviews

7.3Comfort

7.1Entertainment

6.6Food

8.1Crew

7.7Boarding

Pros +

Cons -

Show reviews that mention

6.0 Okay

Paula, May 2025

DEN-FRA

The seat and leg room was not good. The food and beverage service was good.

2.0 Poor

Jane, May 2025

SFO-LHR

Liked fold flat bed. Didn’t like having no window. Didn’t like poor choice of food and being served dinner very late, hours after take off of a 7:40pm flight. Servers not friendly. Food horrible in business class.

10.0 Wonderful

Verified traveler, May 2025

PBI-ORD

Excellent flight

10.0 Wonderful

Verified traveler, May 2025

SFO-HKG

only food wasn’t good

10.0 Wonderful

Verified traveler, May 2025

IAD-SFO

excellent

8.0 Very good

Verified traveler, May 2025

YUL-IAD

Very nice and clean plane. Transit time between flights was tight though

10.0 Wonderful

Mohammad Hassan Mirzai, May 2025

HKG-SFO

I needed to make changes to my flights. When I called customer service, they assisted me with care professionalism.

8.0 Very good

Verified traveler, Apr 2025

XNA-DEN

Everything

10.0 Wonderful

David, Apr 2025

DEN-FLL

No issues, great flight, great crew

10.0 Wonderful

Vincenzo, Apr 2025

IAD-TYS

Friendly crew, all very smooth

Everything you need to know for your flight from Orlando Airport to Chicago

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Other airlines flying from Orlando Airport to Chicago

Spirit Airlines flights from Orlando Airport to Chicago

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$87 Find Cheap United Airlines Flights from Orlando Airport to Chicago

Search hundreds of travel sites at once for deals on United Airlines flights from Orlando Airport to Chicago

Cheap United Airlines Flight Deals from Orlando Airport to Chicago

Recent round-trip United Airlines flight deals from Orlando Airport to Chicago

Recent one-way United Airlines flight deals from Orlando Airport to Chicago

Recent last minute United Airlines flight deals from Orlando Airport to Chicago

Recent direct United Airlines flight deals from Orlando Airport to Chicago

Good to know

When to Book Flights with United Airlines from Orlando Airport to Chicago

FAQs for flying to Chicago with United Airlines

How far in advance should I book tickets for a flight with United Airlines from Orlando Airport to Chicago?

Is United Airlines the cheapest airline to fly with from Orlando Airport to Chicago?

What is the cheapest United Airlines flight from Orlando Airport to Chicago?

Does United Airlines fly direct to Chicago from Orlando Airport?

What’s the cheapest day of the week to fly from Orlando Airport to Chicago with United Airlines?

What’s the cheapest month to fly from Orlando Airport to Chicago with United Airlines?

United Airlines Customer Reviews

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Everything you need to know for your flight from Orlando Airport to Chicago

Other airlines flying from Orlando Airport to Chicago

Flights from the other most popular airlines that fly from Orlando Airport to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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Top United Airlines flights

The most popular destinations for flights with United Airlines according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.