Flights from Orlando to Chicago

Search and find cheap flights from Orlando to Chicago (United States, North America)
Search and find cheap flights from Orlando to Chicago (United States, North America)

Looking for the best tickets for Orlando to Chicago?

Look no more. We’ve gone through the latest 1,019,106 fares to bring you all the insights you could possibly want.
Expect to pay
141 USD for flights from Orlando to Chicago leaving on 3/1/2017 and returning on 3/24/2017
Low 76 USD
141 USD
High 308 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Orlando — Chicago is approximately 59 days to departure.
Normally the best deals on Orlando to Chicago flights are available 1 to 2 months prior to departure.
Days before departure
Best month
Cheapest time of year to fly to Chicago from Orlando is January and February. Most expensive are November and December.
Orlando to Chicago flights are currently cheapest between March and March.
Impact on price
Cheapest airline
According to our data, Spirit Airlines, Frontier Airlines and Delta Air Lines are the cheapest airlines to fly this route.
Popular airlines for this route are Spirit Airlines, Frontier Airlines and Delta Air Lines.
Impact on price (additional fees may apply)
Spirit Airlines
+6%
Frontier Airlines
+9%
Delta Air Lines
+15%
Major US Carrier
+20%
American Airlines
+26%
US Airways
+27%
Best time to fly
Orlando to Chicago flights are approximately 7% more expensive in the noon than in the morning.
It's generally cheaper to take morning flights from Orlando to Chicago.
Impact on price
Cheapest day
Cheapest day of week is typically Wednesday and the most expensive is typically Sunday.
Sunday is normally the most expensive day to fly, whilst Wednesday tends to be the cheapest.
Impact on price
Cheapest route
Fly Orlando Intl - Midway for the best Orlando to Chicago flight prices saving up to 1% on average.
Of the possible routes between Orlando and Chicago best prices tend to be found on Orlando Intl - Midway.
We've got 38 booking sites supporting this and nearby routes.
Impact on price
Orlando Intl-Midway
+0%
Orlando Intl-O'Hare Intl
+2%
Direct flights
There are direct flights from Herndon to Chicago all week with a flight time of 2 hours 48 minutes.
Direct flights available: 369 PER WEEK
Popular non-direct routes for this connection are Orlando Intl - Pittsburgh Intl - Midway - Midway, Orlando Intl - Raleigh Durham - Midway and Orlando Intl - Douglas - O'Hare Intl.
You can fly from Herndon to Chicago indirect via Pittsburgh Intl, Raleigh Durham or Douglas.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Get there quickly

Direct flights to Chicago from Orlando
Return trip
Jan 22 - Jan 27
134 USD
CFEDreamsUS
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 49min
Direct
ORL ORL
Return trip
Jan 22 - Jan 29
141 USD
CheapTickets
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 49min
Direct
ORL ORL
Return trip
Jan 22 - Jan 28
141 USD
CheapTickets
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 49min
Direct
ORL ORL

Go right away

Last minute flights from Orlando to Chicago
Return trip
Jan 22 - Jan 27
134 USD
CFEDreamsUS
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 49min
Direct
ORL ORL
Return trip
Jan 22 - Jan 29
141 USD
CheapTickets
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 49min
Direct
ORL ORL
Return trip
Jan 22 - Jan 28
141 USD
CheapTickets
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 49min
Direct
ORL ORL

Go for less - experience more

Cheap flights from Orlando to Chicago
Return trip
Feb 8 - Feb 13
75 USD
FlyFarUS
ORL ORL
3h 7min
Direct
CHI CHI
CHI CHI
2h 51min
Direct
ORL ORL
Return trip
Feb 9 - Feb 12
79 USD
CFEDreamsUS
ORL ORL
3h 7min
Direct
CHI CHI
CHI CHI
2h 51min
Direct
ORL ORL
Return trip
Feb 10 - Feb 12
79 USD
CFEDreamsUS
ORL ORL
3h 7min
Direct
CHI CHI
CHI CHI
2h 51min
Direct
ORL ORL

Coming or going?

Cheap flights from Chicago to Orlando
Return trip
Jan 22 - Feb 3
74 USD
CFEDreamsUS
CHI CHI
2h 43min
Direct
ORL ORL
ORL ORL
2h 58min
Direct
CHI CHI
Return trip
Jan 22 - Feb 2
92 USD
EDreamsUS
CHI CHI
2h 49min
Direct
ORL ORL
ORL ORL
2h 58min
Direct
CHI CHI
Return trip
Jan 22 - Feb 5
107 USD
CFEDreamsUS
CHI CHI
2h 43min
Direct
ORL ORL
ORL ORL
2h 58min
Direct
CHI CHI

Weather forecast for Chicago

Going soon? Be prepared for the weather in Chicago.

Friday, Friday, January 20, 2017

6°C
4°C

Saturday, Saturday, January 21, 2017

12°C
5°C

Sunday, Sunday, January 22, 2017

8°C
-1°C

Monday, Monday, January 23, 2017

5°C
1°C

Tuesday, Tuesday, January 24, 2017

6°C
2°C

Wednesday, Wednesday, January 25, 2017

4°C
-1°C

Thursday, Thursday, January 26, 2017

2°C
-2°C

Friday, Friday, January 27, 2017

1°C
-3°C

Saturday, Saturday, January 28, 2017

1°C
-4°C

Sunday, Sunday, January 29, 2017

-1°C
-5°C

So what's it going to cost once you're in Chicago

Compare the costs of everyday items in Orlando and Chicago
CAPPUCCINO
Regular
Orlando
4.16 USD
5%
Chicago
3.96 USD
Cappuccino is 4.9% cheaper in Chicago than Orlando
MEAL
Inexpensive
Orlando
15.04 USD
%
Chicago
15.04 USD
Meal is 0% cheaper in Chicago than Orlando
MILK
1 liter
Orlando
3.68 USD
19%
Chicago
2.98 USD
Milk is 19% cheaper in Chicago than Orlando
BUS
One-way ticket
Orlando
2.01 USD
-12%
Chicago
2.25 USD
Bus is 12% more expensive in Chicago than Orlando
MOVIE THEATER
1 ticket
Orlando
11.28 USD
-7%
Chicago
12.03 USD
movie theater is 6.7% more expensive in Chicago than Orlando
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