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Business Class Flight Deals from Houston to Chicago from $316

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Top flight deals from leading airlines:

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Free cancellation for many rates

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Stops

  • Nonstop
    from $613
  • Up to 1 stop
    $623

Airlines

  • Alaska Airlines
    $1143
  • American Airlines
    $613
  • Hawaiian Airlines
    $1171

Cabin Class

  • First
    $613

Departure Airports

  • George Bush Intercontinental Houston Airport
    $613
  • William P Hobby Airport
    $623

Arrival Airports

  • Chicago O Hare Airport
    $613

Layover Airports

  • Charlotte Douglas International Airport
    $623
  • Dallas Fort Worth International Airport
    $623
  • Portland International Airport
    $1143
  • Seattle Tacoma International Airport
    $1143

Best Price. GUARANTEED.

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

05/30/25

IAH
2h 53m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 52m
Direct

06/06/25

IAH
$613
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
2h 42m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 52m
Direct

06/06/25

IAH
$613
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

HOU
5h 25m
DFW

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 52m
Direct

06/06/25

IAH
$623
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
6h 32m
CLT

05/31/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 52m
Direct

06/06/25

IAH
$623
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
5h 27m
DFW

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 52m
Direct

06/06/25

IAH
$623
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
2h 42m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 39m
Direct

06/06/25

IAH
$646
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
2h 42m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 35m
Direct

06/06/25

IAH
$646
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
2h 53m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 39m
Direct

06/06/25

IAH
$646
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
2h 42m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 56m
Direct

06/06/25

IAH
$646
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
2h 53m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 35m
Direct

06/06/25

IAH
$646
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

HOU
5h 25m
DFW

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 56m
Direct

06/06/25

IAH
$656
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
2h 42m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
5h 34m
CLT

06/06/25

IAH
$656
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
6h 32m
CLT

05/31/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 39m
Direct

06/06/25

IAH
$656
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
2h 42m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
4h 43m
DFW

06/06/25

HOU
$656
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
2h 53m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
5h 5m
DFW

06/06/25

IAH
$656
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
2h 53m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
4h 43m
DFW

06/06/25

HOU
$656
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

HOU
5h 25m
DFW

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 39m
Direct

06/06/25

IAH
$656
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
5h 27m
DFW

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 35m
Direct

06/06/25

IAH
$656
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
2h 42m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
5h 5m
DFW

06/06/25

IAH
$656
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
6h 32m
CLT

05/31/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 35m
Direct

06/06/25

IAH
$656
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

HOU
5h 25m
DFW

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 35m
Direct

06/06/25

IAH
$656
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
6h 32m
CLT

05/31/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
2h 56m
Direct

06/06/25

IAH
$656
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

IAH
2h 53m
Direct

05/30/25

ORD
American Airlines Logo
American Airlines

06/06/25

ORD
5h 34m
CLT

06/06/25

IAH
$656
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/30/25

IAH
19h 14m
PDX

05/31/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/06/25

ORD
10h 29m
SEA

06/07/25

IAH
$1143
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/30/25

IAH
19h 14m
PDX

05/31/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/06/25

ORD
12h 22m
SEA

06/07/25

IAH
$1143
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

05/30/25

IAH
19h 14m
PDX

05/31/25

ORD
Hawaiian Airlines Logo
Hawaiian Airlines

06/06/25

ORD
10h 29m
SEA

06/07/25

IAH
$1171
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/30/25

IAH
19h 14m
PDX

05/31/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/06/25

ORD
13h 59m
SEA

06/06/25

IAH
$1178
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

05/30/25

IAH
19h 14m
PDX

05/31/25

ORD
Hawaiian Airlines Logo
Hawaiian Airlines

06/06/25

ORD
13h 59m
SEA

06/06/25

IAH
$1206
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

05/30/25

IAH
12h 55m
SEA

05/30/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/06/25

ORD
10h 29m
SEA

06/07/25

IAH
$1283
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

05/30/25

IAH
12h 55m
SEA

05/30/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/06/25

ORD
12h 22m
SEA

06/07/25

IAH
$1283
Free cancellation within 83 hours of booking

Top Deals on flights Business Class from Houston to Chicago

Houston, US (HOU) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

IAH
6h 32m
CLT

May 30

ORD

as low as

$316

Houston, US (HOU) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

IAH
2h 42m
Direct

May 29

ORD

as low as

$358

Houston, US (HOU) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

IAH
2h 49m
Direct

May 29

ORD

as low as

$431

Houston, US (HOU) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

IAH
2h 43m
Direct

May 29

ORD

as low as

$431

Houston, US (HOU) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

HOU
4h 34m
DFW

May 29

ORD

as low as

$441

Houston, US (HOU) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

IAH
14h 7m
CLT

May 30

ORD

as low as

$494

Houston, US (HOU) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

IAH
16h 11m
CLT

May 30

ORD

as low as

$494

Houston, US (HOU) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

May 29

IAH
19h 14m
PDX

May 30

ORD

as low as

$621

Houston, US (HOU) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

May 29

IAH
17h 59m
SEA

May 29

ORD

as low as

$622

Houston, US (HOU) - Chicago, US (CHI)

Hawaiian Airlines Logo
Hawaiian Airlines

May 29

IAH
19h 14m
PDX

May 30

ORD

as low as

$635

Houston, US (HOU) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

May 29

IAH
10h 26m
SEA

May 30

ORD

as low as

$652

Houston, US (HOU) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

May 29

IAH
12h 55m
SEA

May 29

ORD

as low as

$652

Frequently Asked Questions

Are there convenient layover flights from Houston to Chicago?
Yes, there are convenient layover flights from Houston to Chicago. Notably, one-stop flights include Frontier Airlines at $157, Spirit Airlines at $185, Delta Air Lines at $210, United Airlines at $258, and American Airlines at $287. No two-stop flights are necessary given the availability of non-stop options.
What are the most convenient layover airports for the flight?
The most convenient layover airports for your flight include Hartsfield Jackson Atlanta International Airport, Dallas Fort Worth International Airport, Minneapolis-St Paul International/Wold-Chamberlain Airport, Detroit Metropolitan Airport, and Miami International Airport.
What is the cheapest and fastest flight from Houston to Chicago?
The cheapest flight is with Frontier Airlines at $112, 2h 37m. The fastest flight is also with Frontier Airlines at $133, 2h 33m. Airlines: Frontier - $112, $133.
What are all possible destination arrival airports?
The possible destination arrival airports from Houston to Chicago are Chicago Midway Airport and Chicago O'Hare Airport.
What is the time difference between destination and arrival?
Chicago is one hour ahead of Houston. If your flight from Houston arrives in Chicago, adjust your clock forward by one hour upon arrival.
Is there a direct flight from Houston to Chicago?
Yes, there are direct flights available from Houston to Chicago. Frontier Airlines offers non-stop flights at prices of $112 and $133, with flight times of 2 hours 37 minutes and 2 hours 33 minutes, respectively. Spirit Airlines and United Airlines also provide non-stop flights at higher prices.