background

Flight Deals from Orlando International Airport to Chicago O Hare Airport from $39

Fly where?

Top flight deals from leading airlines:

UA LogoQR LogoSQ LogoNH LogoEK LogoJL LogoTK Logo

... and +100s more

Change Your Mind? No Problem

Cancel within 24 hours for a full refund—no questions asked.

Price Drop Protection

We’ll refund the difference if the price drops before you fly.

No Surprises at Checkout

The prices shown are exactly what you pay, with no hidden taxes or fees.

24/7 Support

Expert travel agents, ready to help anytime by phone, chat, or email.

Stops

  • Nonstop
    from $248
  • Up to 1 stop
    $303
  • Up to 2 stops
    $337

Airlines

  • American Airlines
    $298
  • United Airlines
    $248

Cabin Class

  • Economy
    $248

Departure Airports

  • Orlando International Airport
    $248

Arrival Airports

  • Chicago O Hare Airport
    $248

Layover Airports

  • Charlotte Douglas International Airport
    $303
  • Detroit Metropolitan Airport
    $337
  • New York LaGuardia Airport
    $337
  • Newark Liberty Airport
    $364
  • Washington Dulles Airport
    $342
United Airlines Logo
4:35 pm – 6:45 pm
Orlando(MCO)Chicago(ORD)
MCO - ORD · 2h 10m
20 Feb
2h 10m
20 Feb
nonstop
United Airlines Logo
1:00 pm – 4:52 pm
Chicago(ORD)Orlando(MCO)
ORD - MCO · 3h 52m
22 Feb
3h 52m
22 Feb
nonstop
$248
United Airlines Logo
8:43 pm – 11:00 pm
Orlando(MCO)Chicago(ORD)
MCO - ORD · 2h 17m
26 Feb
2h 17m
26 Feb
nonstop
United Airlines Logo
9:00 am – 12:45 pm
Chicago(ORD)Orlando(MCO)
ORD - MCO · 3h 45m
1 Mar
3h 45m
1 Mar
nonstop
$248
American Airlines Logo
7:02 am – 9:05 am
Orlando(MCO)Chicago(ORD)
MCO - ORD · 2h 3m
26 Feb
2h 3m
26 Feb
nonstop
American Airlines Logo
1:15 pm – 4:57 pm
Chicago(ORD)Orlando(MCO)
ORD - MCO · 3h 42m
26 Feb
3h 42m
26 Feb
nonstop
$298
American Airlines Logo
7:02 am – 9:05 am
Orlando(MCO)Chicago(ORD)
MCO - ORD · 2h 3m
26 Feb
2h 3m
26 Feb
nonstop
American Airlines Logo
12:05 pm – 5:56 pm
Chicago(ORD)Orlando(MCO)
ORD - MCO · 5h 51m
26 Feb
5h 51m
26 Feb
1 stop
CLT
$303
American Airlines Logo
3:52 pm – 5:55 pm
Orlando(MCO)Chicago(ORD)
MCO - ORD · 2h 3m
26 Feb
2h 3m
26 Feb
nonstop
American Airlines Logo
8:25 pm – 12:57 pm
Chicago(ORD)Orlando(MCO)
ORD - MCO · 16h 32m
26 Feb
16h 32m
26 Feb
2 stops
DTW, LGA
$337
United Airlines Logo
9:00 am – 2:20 pm
Orlando(MCO)Chicago(ORD)
MCO - ORD · 5h 20m
20 Feb
5h 20m
20 Feb
1 stop
IAD
United Airlines Logo
10:35 am – 2:25 pm
Chicago(ORD)Orlando(MCO)
ORD - MCO · 3h 50m
22 Feb
3h 50m
22 Feb
nonstop
$342
United Airlines Logo
9:00 am – 2:38 pm
Orlando(MCO)Chicago(ORD)
MCO - ORD · 5h 38m
26 Feb
5h 38m
26 Feb
1 stop
EWR
United Airlines Logo
7:45 pm – 11:45 pm
Chicago(ORD)Orlando(MCO)
ORD - MCO · 4h
1 Mar
4h
1 Mar
nonstop
$364
American Airlines Logo
1:53 pm – 5:54 pm
Orlando(MCO)Chicago(ORD)
MCO - ORD · 4h 1m
26 Feb
4h 1m
26 Feb
1 stop
CLT
American Airlines Logo
8:25 pm – 12:57 pm
Chicago(ORD)Orlando(MCO)
ORD - MCO · 16h 32m
26 Feb
16h 32m
26 Feb
2 stops
DTW, LGA
$421
United Airlines Logo
7:00 pm – 11:43 pm
Orlando(MCO)Chicago(ORD)
MCO - ORD · 4h 43m
20 Feb
4h 43m
20 Feb
1 stop
IAD
United Airlines Logo
10:48 am – 6:07 pm
Chicago(ORD)Orlando(MCO)
ORD - MCO · 7h 19m
22 Feb
7h 19m
22 Feb
1 stop
EWR
$471
United Airlines Logo
9:50 am – 11:53 am
Orlando(MCO)Chicago(ORD)
MCO - ORD · 2h 3m
6 Mar
2h 3m
6 Mar
nonstop
United Airlines Logo
7:45 pm – 11:45 pm
Chicago(ORD)Orlando(MCO)
ORD - MCO · 4h
8 Mar
4h
8 Mar
nonstop
$486
United Airlines Logo
6:50 pm – 8:51 pm
Orlando(MCO)Chicago(ORD)
MCO - ORD · 2h 1m
7 Mar
2h 1m
7 Mar
nonstop
United Airlines Logo
6:00 am – 9:40 am
Chicago(ORD)Orlando(MCO)
ORD - MCO · 3h 40m
8 Mar
3h 40m
8 Mar
nonstop
$486
United Airlines Logo
11:11 am – 6:39 pm
Orlando(MCO)Chicago(ORD)
MCO - ORD · 7h 28m
26 Feb
7h 28m
26 Feb
1 stop
IAD
United Airlines Logo
7:10 am – 4:35 pm
Chicago(ORD)Orlando(MCO)
ORD - MCO · 9h 25m
1 Mar
9h 25m
1 Mar
1 stop
EWR
$493
United Airlines Logo
3:20 pm – 11:42 pm
Orlando(MCO)Chicago(ORD)
MCO - ORD · 8h 22m
6 Mar
8h 22m
6 Mar
1 stop
EWR
United Airlines Logo
6:00 pm – 9:53 pm
Chicago(ORD)Orlando(MCO)
ORD - MCO · 3h 53m
7 Mar
3h 53m
7 Mar
nonstop
$496
United Airlines Logo
9:50 am – 11:53 am
Orlando(MCO)Chicago(ORD)
MCO - ORD · 2h 3m
7 Mar
2h 3m
7 Mar
nonstop
United Airlines Logo
8:55 am – 4:33 pm
Chicago(ORD)Orlando(MCO)
ORD - MCO · 7h 38m
8 Mar
7h 38m
8 Mar
1 stop
IAD
$496
United Airlines Logo
1:51 pm – 6:33 pm
Orlando(MCO)Chicago(ORD)
MCO - ORD · 4h 42m
6 Mar
4h 42m
6 Mar
1 stop
IAD
United Airlines Logo
8:55 am – 4:33 pm
Chicago(ORD)Orlando(MCO)
ORD - MCO · 7h 38m
8 Mar
7h 38m
8 Mar
1 stop
IAD
$506

Top Deals on flights from Orlando International Airport to Chicago O Hare Airport

Orlando, US (ORL) - Chicago, US (CHI)

 Logo

Dec 5

MCO
2h 29m
Direct

Dec 5

ORD

as low as

$39

Orlando, US (ORL) - Chicago, US (CHI)

 Logo

Dec 5

MCO
2h 5m
Direct

Dec 5

ORD

as low as

$40

Orlando, US (ORL) - Chicago, US (CHI)

 Logo

Dec 5

MCO
12h 16m
IAH

Dec 5

ORD

as low as

$66

Orlando, US (ORL) - Chicago, US (CHI)

 Logo

Feb 28

MCO
5h 49m
MSY

Mar 1

ORD

as low as

$75

Orlando, US (ORL) - Chicago, US (CHI)

 Logo

Dec 6

MCO
6h 27m
FLL

Dec 6

ORD

as low as

$75

Orlando, US (ORL) - Chicago, US (CHI)

 Logo

Dec 12

MCO
7h 39m
DFW

Dec 12

ORD

as low as

$75

Orlando, US (ORL) - Chicago, US (CHI)

 Logo

Nov 7

MCO
4h 29m
ATL

Nov 8

ORD

as low as

$76

Orlando, US (ORL) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Dec 5

MCO
2h 2m
Direct

Dec 5

ORD

as low as

$79

Orlando, US (ORL) - Chicago, US (CHI)

 Logo

Dec 11

MCO
5h 26m
ATL

Dec 12

ORD

as low as

$98

Orlando, US (ORL) - Chicago, US (CHI)

 Logo

Nov 10

MCO
5h 20m
DTW

Nov 10

ORD

as low as

$108

Orlando, US (ORL) - Chicago, US (CHI)

 Logo

Nov 12

MCO
7h 7m
JFK

Nov 12

ORD

as low as

$113

Orlando, US (ORL) - Chicago, US (CHI)

 Logo

Dec 5

MCO
8h 48m
BOS

Dec 5

ORD

as low as

$113

Flights to Chicago

  • Flights
  • North America
  • United States
  • Illinois
  • Chicago
  • Chicago O Hare Airport