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Business Class Flight Deals from Miami to Chicago from $371

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Top flight deals from leading airlines:

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... and +100s more

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Free cancellation for many rates

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

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Stops

  • Nonstop
    from $777
  • Up to 1 stop
    $744

Airlines

  • American Airlines
    $744

Cabin Class

  • First
    $744

Departure Airports

  • Miami International Airport
    $744

Arrival Airports

  • Chicago O Hare Airport
    $744

Layover Airports

  • Charleston Air Force Base-International Airport
    $822
  • Charlotte Douglas International Airport
    $787
  • Hartsfield Jackson Atlanta International Airport
    $822
  • Indianapolis International Airport
    $822
  • Orlando International Airport
    $787
  • Raleigh Durham International Airport
    $744
  • Reagan Washington National Airport
    $822
  • Tampa International Airport
    $787

Best Price. GUARANTEED.

Exclusively for Priceline Members
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On average save $240 per traveler
American Airlines Logo
American Airlines

05/29/25

MIA
3h 28m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
20h 13m
RDU

06/06/25

MIA
$744
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 29m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
3h 8m
Direct

06/05/25

MIA
$777
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 29m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
3h 7m
Direct

06/05/25

MIA
$777
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 28m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
3h 7m
Direct

06/05/25

MIA
$777
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 28m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
3h 8m
Direct

06/05/25

MIA
$777
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 28m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
5h 36m
TPA

06/05/25

MIA
$787
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 29m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
5h 36m
TPA

06/05/25

MIA
$787
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 29m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
5h 42m
CLT

06/05/25

MIA
$787
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 29m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
5h 3m
MCO

06/05/25

MIA
$787
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 28m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
4h 37m
CLT

06/05/25

MIA
$787
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 28m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
5h 42m
CLT

06/05/25

MIA
$787
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 28m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
5h 56m
MCO

06/05/25

MIA
$787
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 29m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
5h 11m
TPA

06/05/25

MIA
$787
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 28m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
5h 3m
MCO

06/05/25

MIA
$787
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 29m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
4h 37m
CLT

06/05/25

MIA
$787
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 28m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
5h 11m
TPA

06/05/25

MIA
$787
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 28m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
5h 4m
CLT

06/06/25

MIA
$787
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 29m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
5h 4m
CLT

06/06/25

MIA
$787
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
3h 29m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
5h 56m
MCO

06/05/25

MIA
$787
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
6h 22m
MCO

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
3h 7m
Direct

06/05/25

MIA
$822
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
6h 16m
DCA

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
3h 8m
Direct

06/05/25

MIA
$822
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
5h 3m
MCO

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
3h 7m
Direct

06/05/25

MIA
$822
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
5h 46m
ATL

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
3h 8m
Direct

06/05/25

MIA
$822
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
6h 5m
CHS

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
3h 8m
Direct

06/05/25

MIA
$822
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
6h 5m
CHS

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
3h 7m
Direct

06/05/25

MIA
$822
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
6h 16m
DCA

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
3h 7m
Direct

06/05/25

MIA
$822
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
5h 11m
IND

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
3h 8m
Direct

06/05/25

MIA
$822
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
5h 23m
DCA

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
3h 7m
Direct

06/05/25

MIA
$822
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
5h 46m
ATL

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
3h 7m
Direct

06/05/25

MIA
$822
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

MIA
5h 23m
DCA

05/29/25

ORD
American Airlines Logo
American Airlines

06/05/25

ORD
3h 8m
Direct

06/05/25

MIA
$822
Free cancellation within 83 hours of booking

Top Deals on flights Business Class from Miami to Chicago

Miami, US (MIA) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

MIA
3h 28m
Direct

May 29

ORD

as low as

$371

Miami, US (MIA) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

MIA
6h 21m
CVG

May 29

ORD

as low as

$377

Miami, US (MIA) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

MIA
6h 18m
PIT

May 29

ORD

as low as

$416

Miami, US (MIA) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

MIA
5h 23m
DCA

May 29

ORD

as low as

$416

Miami, US (MIA) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

MIA
6h 33m
TPA

May 29

ORD

as low as

$416

Miami, US (MIA) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

MIA
5h 3m
MCO

May 29

ORD

as low as

$416

Miami, US (MIA) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

MIA
6h 6m
LGA

May 29

ORD

as low as

$461

Miami, US (MIA) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

MIA
6h 42m
RDU

May 29

ORD

as low as

$461

Miami, US (MIA) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

MIA
6h 22m
PHL

May 29

ORD

as low as

$538

Miami, US (MIA) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

MIA
5h 54m
CLT

May 29

ORD

as low as

$538

Miami, US (MIA) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

MIA
5h 45m
BNA

May 29

ORD

as low as

$551

Miami, US (MIA) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

MIA
6h 20m
STL

May 29

ORD

as low as

$861

Frequently Asked Questions

What is the cheapest and fastest flight from Miami to Chicago?
The cheapest flight is with Spirit Airlines for $107, 2h 26m. The fastest flight is with American Airlines for $268, 2h 25m.
What are all possible destination arrival airports?
The possible destination arrival airport for your flight is Chicago O'Hare Airport.
What is the time difference between destination and arrival?
The time difference between Miami and Chicago is one hour, with Chicago being one hour behind Miami.
Is there a direct flight from Miami to Chicago?
Yes, there are direct flights from Miami to Chicago. Spirit Airlines offers the cheapest flight at $107, and American Airlines offers the fastest flight at $268. United Airlines also has a direct flight at $258.
Are there convenient layover flights from Miami to Chicago?
Yes, there are convenient one-stop flights available. They include Delta Air Lines at $216, JetBlue at $216, Frontier Airlines at $227, American Airlines at $307, and United Airlines at $319.
What are the most convenient layover airports for my flight?
For your flight from Miami to Chicago, convenient layover airports include Hartsfield Jackson Atlanta International Airport, New York John F Kennedy Airport, New York LaGuardia Airport, and George Bush Intercontinental Houston Airport.