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Business Class Flight Deals from Orlando to Chicago O Hare Airport from $406

Bundle + Save

Bundle + Save

Top flight deals from leading airlines:

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... and +100s more

Customer-First Commitment

Free cancellation for many rates

Best Price Guarantee

If a VIP member finds a better price elsewhere, we'll refund up to 200% of the difference

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VIP member priority support for seamless bookings and exclusive travel benefits

Help 24/7

We’re always here for you - reach us 24 hours a day, 7 days a week

Stops

  • Nonstop
    from $841
  • Up to 1 stop
    $826

Airlines

  • American Airlines
    $826

Cabin Class

  • First
    $826

Departure Airports

  • Orlando International Airport
    $826

Arrival Airports

  • Chicago O Hare Airport
    $826

Layover Airports

  • Charlotte Douglas International Airport
    $851
  • New York LaGuardia Airport
    $851
  • Reagan Washington National Airport
    $826

Best Price. GUARANTEED.

Exclusively for Priceline Members
Tired of searching? Book now!
We'll refund the difference if you find a lower price.

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On average save $240 per traveler
American Airlines Logo
American Airlines

05/30/25

MCO
11h 11m
DCA

05/31/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 35m
Direct

06/06/25

MCO
$826
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 10m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 41m
Direct

06/06/25

MCO
$841
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 5m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 43m
Direct

06/06/25

MCO
$841
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 7m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 38m
Direct

06/06/25

MCO
$841
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 7m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 35m
Direct

06/06/25

MCO
$841
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 5m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 51m
Direct

06/06/25

MCO
$841
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 7m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 43m
Direct

06/06/25

MCO
$841
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 5m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 41m
Direct

06/06/25

MCO
$841
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 7m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 41m
Direct

06/06/25

MCO
$841
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 10m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 38m
Direct

06/06/25

MCO
$841
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 5m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 35m
Direct

06/06/25

MCO
$841
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 5m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 38m
Direct

06/06/25

MCO
$841
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 10m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 35m
Direct

06/06/25

MCO
$841
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 10m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 43m
Direct

06/06/25

MCO
$841
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
5h 25m
CLT

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 35m
Direct

06/06/25

MCO
$851
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
5h 1m
CLT

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 38m
Direct

06/06/25

MCO
$851
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 5m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
4h 34m
CLT

06/06/25

MCO
$851
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
5h 58m
LGA

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 35m
Direct

06/06/25

MCO
$851
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
5h 58m
LGA

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 38m
Direct

06/06/25

MCO
$851
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
5h 58m
LGA

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 43m
Direct

06/06/25

MCO
$851
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
5h 1m
CLT

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 35m
Direct

06/06/25

MCO
$851
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
5h 58m
LGA

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 41m
Direct

06/06/25

MCO
$851
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 10m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
4h 13m
CLT

06/06/25

MCO
$851
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
5h 1m
CLT

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 51m
Direct

06/06/25

MCO
$851
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
5h 1m
CLT

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 43m
Direct

06/06/25

MCO
$851
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
5h 18m
CLT

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 38m
Direct

06/06/25

MCO
$851
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
5h 18m
CLT

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 35m
Direct

06/06/25

MCO
$851
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 10m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
4h 34m
CLT

06/06/25

MCO
$851
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
3h 7m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
4h 34m
CLT

06/06/25

MCO
$851
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

MCO
5h 38m
CLT

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 38m
Direct

06/06/25

MCO
$851
Free cancellation within 83 hours of booking

Top Deals on flights Business Class from Orlando to Chicago O Hare Airport

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

American Airlines Logo
American Airlines

May 29

MCO
3h 5m
Direct

May 29

ORD

as low as

$406

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

American Airlines Logo
American Airlines

May 29

MCO
3h 5m
Direct

May 29

ORD

as low as

$406

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

American Airlines Logo
American Airlines

May 29

MCO
3h 5m
Direct

May 29

ORD

as low as

$406

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

American Airlines Logo
American Airlines

May 29

MCO
5h 25m
CLT

May 29

ORD

as low as

$416

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

American Airlines Logo
American Airlines

May 29

MCO
6h 12m
LGA

May 29

ORD

as low as

$416

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

American Airlines Logo
American Airlines

May 29

MCO
5h 25m
CLT

May 29

ORD

as low as

$416

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

American Airlines Logo
American Airlines

May 29

MCO
5h 34m
CLT

May 30

ORD

as low as

$416

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

American Airlines Logo
American Airlines

May 29

MCO
7h 43m
DCA

May 29

ORD

as low as

$416

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

American Airlines Logo
American Airlines

May 29

MCO
6h 20m
DFW

May 29

ORD

as low as

$488

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

American Airlines Logo
American Airlines

May 29

MCO
5h 40m
PHL

May 29

ORD

as low as

$488

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

American Airlines Logo
American Airlines

May 29

MCO
15h 7m
MIA
LGA

May 30

ORD

as low as

$538

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

 Logo

May 29

MCO
14h 59m
SEA

May 29

ORD

as low as

$1317