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
199 USD for flights from Orlando to Chicago leaving on 8/8/2017 and returning on 9/1/2017
Low 97 USD
199 USD
High 309 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for Orlando — Chicago is approximately 58 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 June and December.
Orlando to Chicago flights are currently cheapest between August and September.
Impact on price
Cheapest airline
According to our data, Frontier Airlines, Delta Air Lines and Spirit Airlines are the cheapest airlines to fly this route.
momondo users most frequently choose to fly from Orlando to Chicago with either Frontier Airlines, Delta Air Lines or Spirit Airlines.
Impact on price (additional fees may apply)
Frontier Airlines
+7%
Delta Air Lines
+11%
Spirit Airlines
+13%
Major US Carrier
+16%
American Airlines
+22%
Southwest Airlines
+22%
Best time to fly
Orlando to Chicago flights are approximately 4% more expensive in the noon than in the morning.
Noon flights tend to be the most expensive.
Impact on price
Cheapest day
Sunday is normally the most expensive day to fly, whilst Tuesday tends to be the cheapest.
Cheapest day of week is typically Tuesday and the most expensive is typically Sunday.
Impact on price
Cheapest route
Fly Orlando Intl - Midway for the best Orlando to Chicago flight prices saving up to 1% on average.
Orlando Intl - Midway tends to be 1% cheaper than Orlando Intl - O'Hare Intl.
We scan 44 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: 308 PER WEEK
Popular non-direct routes for this connection are Orlando Intl - Dallas Ft Worth - O'Hare Intl, Orlando Intl - Hartsfield Jackson - O'Hare Intl and Orlando Intl - Saint Paul Intl - O'Hare Intl.
You can fly from Herndon to Chicago indirect via Dallas Ft Worth, Hartsfield Jackson or 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
Jun 28 - Jul 6
201 USD
EDreamsUS
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
3h 4min
Direct
ORL ORL
Return trip
Jun 29 - Jun 30
234 USD
EDreamsUS
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 49min
Direct
ORL ORL
Return trip
Jun 28 - Jun 30
238 USD
CFEDreamsUS
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 39min
Direct
ORL ORL

Go right away

Last minute flights from Orlando to Chicago
Return trip
Jun 29 - Jul 3
178 USD
FlightNetworkUS
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 39min
Direct
ORL ORL
Return trip
Jun 29 - Jul 2
219 USD
CFEDreamsUS
ORL ORL
3h 14min
Direct
CHI CHI
CHI CHI
2h 49min
Direct
ORL ORL
Return trip
Jun 28 - Jun 30
238 USD
CFEDreamsUS
ORL ORL
3h 5min
Direct
CHI CHI
CHI CHI
2h 39min
Direct
ORL ORL

Go for less - experience more

Cheap flights from Orlando to Chicago
Return trip
Jul 12 - Jul 19
114 USD
CheapTickets
ORL ORL
3h 12min
Direct
CHI CHI
CHI CHI
3h 4min
Direct
ORL ORL
Return trip
Jul 13 - Jul 20
139 USD
Cheapoair
ORL ORL
3h 12min
Direct
CHI CHI
CHI CHI
3h 4min
Direct
ORL ORL
Return trip
Jul 12 - Jul 26
155 USD
FlyFarUS
ORL ORL
2h 40min
Direct
CHI CHI
CHI CHI
2h 30min
Direct
ORL ORL

Coming or going?

Cheap flights from Chicago to Orlando
Return trip
Jun 28 - Jul 12
145 USD
CFFlyFarUS
CHI CHI
2h 35min
Direct
ORL ORL
ORL ORL
3h 5min
Direct
CHI CHI
Return trip
Jun 28 - Jul 4
166 USD
CrystalTravelUS
CHI CHI
2h 51min
Direct
ORL ORL
ORL ORL
2h 53min
Direct
CHI CHI
Return trip
Jun 28 - Jul 13
170 USD
CFFlyFarUS
CHI CHI
2h 30min
Direct
ORL ORL
ORL ORL
3h 5min
Direct
CHI CHI

Weather forecast for Chicago

Going soon? Be prepared for the weather in Chicago.

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
3.94 USD
-1%
Chicago
3.96 USD
Cappuccino is 0.57% more expensive in Chicago than Orlando
MEAL
Inexpensive
Orlando
15.15 USD
1%
Chicago
15.07 USD
Meal is 0.52% cheaper in Chicago than Orlando
MILK
1 liter
Orlando
3.69 USD
20%
Chicago
2.96 USD
Milk is 20% cheaper in Chicago than Orlando
BUS
One-way ticket
Orlando
2.02 USD
-12%
Chicago
2.26 USD
Bus is 12% more expensive in Chicago than Orlando
MOVIE THEATER
1 ticket
Orlando
12.12 USD
1%
Chicago
12.06 USD
movie theater is 0.56% cheaper in Chicago than Orlando
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