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
141 USD for flights from Orlando to Chicago leaving on 11/29/2017 and returning on 12/22/2017
Low 86 USD
141 USD
High 344 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Orlando — Chicago is approximately 40 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 February and October. Most expensive are June and July.
Currently the cheapest days to fly this route are between November and December.
Impact on price
Cheapest airline
According to our data, Delta Air Lines, Frontier Airlines and Southwest Airlines are the cheapest airlines to fly this route.
Popular airlines for this route are Delta Air Lines, Frontier Airlines and Southwest Airlines.
Impact on price (additional fees may apply)
Delta Air Lines
+6%
Frontier Airlines
+10%
Southwest Airlines
+12%
Spirit Airlines
+14%
American Airlines
+22%
Major US Carrier
+23%
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 0% on average.
Of the possible routes between Orlando and Chicago best prices tend to be found on Orlando Intl - Midway.
We've got 47 booking sites supporting this and nearby routes.
Impact on price
Orlando Intl-Midway
+0%
Orlando Intl-O'Hare Intl
+1%
Direct flights
There are direct flights from Herndon to Chicago all week with a flight time of 2 hours 51 minutes.
Direct flights available: 292 PER WEEK
Popular non-direct routes for this connection are Orlando Intl - Hartsfield Jackson - Midway, Orlando Intl - Dallas Ft Worth - O'Hare Intl and Orlando Intl - Detroit Metro - R Reagan Nat - O'Hare Intl.
Stop-off cities for indirect flights from Herndon to Chicago include Hartsfield Jackson, Dallas Ft Worth and Detroit Metro.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Get there quickly

Direct flights to Chicago from Orlando
Return trip
Oct 23 - Nov 15
111 USD
CFEDreamsUS
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 52min
Direct
ORL ORL
Return trip
Oct 24 - Nov 24
135 USD
CFEDreamsUS
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 41min
Direct
ORL ORL
Return trip
Oct 23 - Oct 26
207 USD
KissAndFlyUS
ORL ORL
2h 59min
Direct
CHI CHI
CHI CHI
2h 40min
Direct
ORL ORL

Go right away

Last minute flights from Orlando to Chicago
Return trip
Oct 25 - Oct 31
75 USD
Smartfares
ORL ORL
3h 1min
Direct
CHI CHI
CHI CHI
2h 50min
Direct
ORL ORL
Return trip
Oct 27 - Oct 29
97 USD
JustAirTicketINT
ORL ORL
2h 58min
Direct
CHI CHI
CHI CHI
2h 40min
Direct
ORL ORL
Return trip
Oct 24 - Nov 24
135 USD
CFEDreamsUS
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 41min
Direct
ORL ORL

Go for less - experience more

Cheap flights from Orlando to Chicago
Return trip
Nov 5 - Nov 10
200 USD
JustAirTicketINT
ORL ORL
4h 51min
1 stop
CHI CHI
CHI CHI
2h 48min
Direct
ORL ORL
Return trip
Nov 5 - Nov 8
203 USD
KiwiUS
ORL ORL
17h 40min
1 stop
CHI CHI
CHI CHI
2h 40min
Direct
ORL ORL
Return trip
Nov 5 - Nov 12
252 USD
Smartfares
ORL ORL
23h 52min
1 stop
CHI CHI
CHI CHI
2h 40min
Direct
ORL ORL

Coming or going?

Cheap flights from Chicago to Orlando
Return trip
Oct 23 - Oct 31
102 USD
ExploreTripDom
CHI CHI
2h 51min
Direct
ORL ORL
ORL ORL
3h 5min
Direct
CHI CHI
Return trip
Oct 23 - Oct 26
115 USD
ExploreTripDom
CHI CHI
2h 38min
Direct
ORL ORL
ORL ORL
2h 59min
Direct
CHI CHI
Return trip
Oct 23 - Oct 27
172 USD
JustAirTicketINT
CHI CHI
5h 5min
1 stop
ORL ORL
ORL ORL
6h 8min
1 stop
CHI CHI

Weather forecast for Chicago

Going soon? Be prepared for the weather in Chicago.

Wednesday, Wednesday, October 18, 2017

17°C
12°C

Thursday, Thursday, October 19, 2017

18°C
12°C

Friday, Friday, October 20, 2017

21°C
15°C

Saturday, Saturday, October 21, 2017

22°C
15°C

Sunday, Sunday, October 22, 2017

16°C
12°C

Monday, Monday, October 23, 2017

17°C
12°C

Tuesday, Tuesday, October 24, 2017

12°C
8°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
3.75 USD
-4%
Chicago
3.91 USD
Cappuccino is 4.4% more expensive in Chicago than Orlando
MEAL
Inexpensive
Orlando
14.52 USD
-3%
Chicago
15.02 USD
Meal is 3.4% more expensive in Chicago than Orlando
MILK
1 liter
Orlando
3.51 USD
14%
Chicago
3.03 USD
Milk is 14% cheaper in Chicago than Orlando
BUS
One-way ticket
Orlando
2 USD
-12%
Chicago
2.25 USD
Bus is 12% more expensive in Chicago than Orlando
MOVIE THEATER
1 ticket
Orlando
12.01 USD
-2%
Chicago
12.26 USD
movie theater is 2.1% more expensive in Chicago than Orlando
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