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 1,274,884 fares to bring you all the insights you could possibly want.
Expect to pay
183 USD for flights from Orlando to Chicago leaving on 10/3/2017 and returning on 10/27/2017
Low 108 USD
183 USD
High 324 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Orlando — Chicago is approximately 39 days to departure.
Orlando to Chicago flights are usually cheapest between 1 and 2 months before departure.
Days before departure
Best month
Cheapest time of year to fly to Chicago from Orlando is January and February. Most expensive are June and July.
The cheapest flights from Orlando to Chicago are currently available between October and October.
Impact on price
Cheapest airline
According to our data, Frontier Airlines, Delta Air Lines and Air Canada Rouge are the cheapest airlines to fly this route.
Frontier Airlines, Delta Air Lines and Air Canada Rouge are the most popular choices flying from Orlando to Chicago.
Impact on price (additional fees may apply)
Frontier Airlines
+8%
Delta Air Lines
+9%
Air Canada Rouge
+11%
Spirit Airlines
+12%
Southwest Airlines
+14%
Major US Carrier
+18%
Best time to fly
Orlando to Chicago flights are approximately 7% more expensive in the noon than in the afternoon.
It's generally cheaper to take afternoon flights from Orlando to Chicago.
Impact on price
Cheapest day
Cheapest day of week is typically Tuesday and the most expensive is typically Sunday.
Sunday is normally the most expensive day to fly, whilst Tuesday 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 scan 49 sites offering flights from Orlando to Chicago to find all the best options.
Impact on price
Orlando Intl-Midway
+0%
Orlando Intl-O'Hare Intl
+3%
Direct flights
There are direct flights from Herndon to Chicago all week with a flight time of 2 hours 51 minutes.
Direct flights available: 321 PER WEEK
Popular non-direct routes for this connection are Orlando Intl - Dallas Ft Worth - O'Hare Intl, Orlando Intl - Hartsfield Jackson - Midway and Orlando Intl - Saint Paul Intl - O'Hare Intl.
Stop-off cities for indirect flights from Herndon to Chicago include Dallas Ft Worth, Hartsfield Jackson and Saint Paul Intl.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Get there quickly

Direct flights to Chicago from Orlando
Return trip
Aug 23 - Aug 30
108 USD
CrystalTravelUS
ORL ORL
2h 58min
Direct
CHI CHI
CHI CHI
2h 45min
Direct
ORL ORL
Return trip
Aug 23 - Aug 25
112 USD
Smartfares
ORL ORL
3h 7min
Direct
CHI CHI
CHI CHI
2h 54min
Direct
ORL ORL
Return trip
Aug 23 - Aug 23
146 USD
FlightNetworkUS
ORL ORL
2h 40min
Direct
CHI CHI
CHI CHI
2h 35min
Direct
ORL ORL

Go right away

Last minute flights from Orlando to Chicago
Return trip
Aug 24 - Aug 25
98 USD
CFEDreamsUS
ORL ORL
3h 7min
Direct
CHI CHI
CHI CHI
2h 54min
Direct
ORL ORL
Return trip
Aug 25 - Aug 27
130 USD
Cheapoair
ORL ORL
3h 7min
Direct
CHI CHI
CHI CHI
2h 54min
Direct
ORL ORL
Return trip
Aug 23 - Aug 23
146 USD
FlightNetworkUS
ORL ORL
2h 40min
Direct
CHI CHI
CHI CHI
2h 35min
Direct
ORL ORL

Go for less - experience more

Cheap flights from Orlando to Chicago
Return trip
Sep 6 - Sep 11
97 USD
Smartfares
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 38min
Direct
ORL ORL
Return trip
Sep 6 - Sep 8
107 USD
FaregeekUSDOM
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 38min
Direct
ORL ORL
Return trip
Sep 6 - Sep 13
107 USD
FaregeekUSDOM
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 38min
Direct
ORL ORL

Coming or going?

Cheap flights from Chicago to Orlando
Return trip
Aug 23 - Aug 24
112 USD
FlyingCOM
CHI CHI
2h 35min
Direct
ORL ORL
ORL ORL
2h 54min
Direct
CHI CHI
Return trip
Aug 24 - Aug 24
118 USD
ExploreTripDom
CHI CHI
2h 54min
Direct
ORL ORL
ORL ORL
3h 7min
Direct
CHI CHI
Return trip
Aug 23 - Aug 27
119 USD
CFFlyFarUS
CHI CHI
2h 54min
Direct
ORL ORL
ORL ORL
2h 40min
Direct
CHI CHI

Weather forecast for Chicago

Going soon? Be prepared for the weather in Chicago.

Thursday, Thursday, August 17, 2017

29°C
19°C

Friday, Friday, August 18, 2017

28°C
18°C

Saturday, Saturday, August 19, 2017

26°C
21°C

Sunday, Sunday, August 20, 2017

29°C
22°C

Monday, Monday, August 21, 2017

30°C
23°C

Tuesday, Tuesday, August 22, 2017

31°C
23°C

Wednesday, Wednesday, August 23, 2017

29°C
22°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
3.96 USD
%
Chicago
3.95 USD
Cappuccino is 0.3% cheaper in Chicago than Orlando
MEAL
Inexpensive
Orlando
14.46 USD
-3%
Chicago
14.96 USD
Meal is 3.4% more expensive in Chicago than Orlando
MILK
1 liter
Orlando
3.67 USD
19%
Chicago
2.98 USD
Milk is 19% cheaper in Chicago than Orlando
BUS
One-way ticket
Orlando
1.99 USD
-13%
Chicago
2.25 USD
Bus is 13% more expensive in Chicago than Orlando
MOVIE THEATER
1 ticket
Orlando
11.97 USD
-4%
Chicago
12.47 USD
movie theater is 4.2% more expensive in Chicago than Orlando
Feedback