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Business Class Flights to Chicago in 2026

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Cheap Business Class Flight Deals to Chicago

Recent business class round-trip flight deals to Chicago

Enter your travel dates to find the best prices.
American Airlines Logo
9:03 am - 10:58 am
JFK
-
ORD
2h 55mnonstop
American Airlines Logo
4:44 pm - 8:19 pm
ORD
-
JFK
2h 35mnonstop
$443American Airlines
Wed, May 6 - Sat, Jun 27
American Airlines Logo
7:10 am - 9:02 am
EWR
-
ORD
2h 52mnonstop
American Airlines Logo
6:51 am - 10:12 am
ORD
-
EWR
2h 21mnonstop
$444American Airlines
Wed, May 6 - Fri, May 8
American Airlines Logo
9:20 pm - 11:48 pm
DFW
-
ORD
2h 28mnonstop
American Airlines Logo
6:04 am - 8:47 am
ORD
-
DFW
2h 43mnonstop
$449American Airlines
Sun, May 3 - Tue, May 5
American Airlines Logo
7:00 am - 10:37 am
DEN
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ORD
2h 37mnonstop
American Airlines Logo
8:45 pm - 10:37 pm
ORD
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DEN
2h 52mnonstop
$450American Airlines
Sat, Mar 28 - Wed, Apr 1
American Airlines Logo
8:14 pm - 10:45 pm
DFW
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ORD
2h 31mnonstop
American Airlines Logo
6:56 pm - 9:40 pm
ORD
-
DFW
2h 44mnonstop
$451American Airlines
Wed, Apr 29 - Sat, May 2
American Airlines Logo
6:00 am - 7:25 am
DCA
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ORD
2h 25mnonstop
American Airlines Logo
6:09 am - 9:00 am
ORD
-
DCA
1h 51mnonstop
$453American Airlines
Wed, Apr 1 - Sun, Apr 5
Alaska Airlines Logo
12:35 am - 6:39 am
SEA
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ORD
4h 04mnonstop
Alaska Airlines Logo
8:48 pm - 11:29 pm
ORD
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SEA
4h 41mnonstop
$541Alaska Airlines
Wed, Apr 15 - Fri, Apr 24
Alaska Airlines Logo
5:49 pm - 11:59 pm
SEA
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ORD
4h 10mnonstop
Alaska Airlines Logo
8:48 pm - 11:29 pm
ORD
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SEA
4h 41mnonstop
$546Alaska Airlines
Wed, Apr 15 - Fri, Apr 24
Alaska Airlines Logo
5:49 pm - 11:59 pm
SEA
-
ORD
4h 10mnonstop
Alaska Airlines Logo
6:00 am - 8:37 am
ORD
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SEA
4h 37mnonstop
$551Alaska Airlines
Wed, Apr 15 - Tue, Apr 21
Multiple Airlines Logo
8:47 pm - 6:40 am
DFW
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ORD
9h 53m
1 stop
Multiple Airlines Logo
8:48 pm - 5:21 pm
ORD
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DFW
44h 33m
2 stops
$9,439Multiple Airlines
Thu, Apr 30 - Sat, May 2

Business Class Flights to Chicago - Travel Insights & Trends

Get data-powered insights and trends for Business Class flights to Chicago to help you craft the best travel plan

What cabin class options are available on United States to Chicago flights?

There are 4 cabin classes available to choose from on United States to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on United States to Chicago flights?

No. A direct flight is the cheapest option for a flight between United States to Chicago.

What is the cheapest airline that flies Business Class from United States to Chicago?

American Airlines and Alaska Airlines are popular carriers operating the cheapest Business Class flights from United States to Chicago

What is the cheapest month to fly Business Class to Chicago?

In general, January is the cheapest month to fly Business Class from United States to Chicago. Due to it being the ‘off-season’ during this time, you can expect Business Class flight prices to be around $402. If you aren’t able to travel during the month of January, then book Business Class flights to Chicago from United States during March instead. Business Class flights to Chicago in March, while not as cheap as those in January, still average around $529.

What is the cheapest day to depart on your Business Class flight to Chicago?

The cheapest day to depart from United States to Chicago is on a Wednesday when prices can be found for as low as $271. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average Business Class ticket price to Chicago on a Sunday is $565.

How long does it take to fly to Chicago?

Average flight duration from United States to Chicago depends on which airport you fly into and out of. Flying from New York to Chicago O'Hare Intl Airport is 2h 41m on average, while flying from Boston to Chicago O'Hare Intl Airport is 2h 53m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

How many flights depart from United States to Chicago on average per day?

As of February 2026, 458 flights take off from United States and land in Chicago each day. The most common flight departure time for this route is 3:00PM, with 43% of daily flights taking off at noon.

How many flights depart from United States to Chicago on average per week?

As of February 2026, 3,209 flights take off from United States and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

What is the cheapest Business Class flight I can find to Chicago?

On average, round trip Business Class flights to Chicago cost $1,210/pp. Prices depend on where you are departing from. For prices as low as $505/pp, depart from New York. The most expensive round trip Business Class flights to Chicago are from Los Angeles.

See prices from:

What airlines fly Business Class to Chicago?

United Airlines is the most popular airline offering Business Class flights to Chicago, with 55% of our users opting to fly with them when traveling to Chicago. Other popular options include American Airlines and Delta. There are a total of 4 different airlines flying to Chicago.

Popular Airlines for Business Class Flights to Chicago

Book reliable Business Class tickets to Chicago from top-rated airlines
AirlineRatingBusiness ClassPrice
DeltaPriceFrom $75First ClassRating
7.9
See reviews
8.1

Boarding

7.9

Comfort

8.5

Crew

7.8

Entertainment

7.2

Food

Reviews

1 / 10
great crew and lunch was very good.
Search Delta flights
United AirlinesPriceFrom $117First ClassRating
7.4
See reviews
7.7

Boarding

7.3

Comfort

8.1

Crew

7.1

Entertainment

6.6

Food

Reviews

1 / 10
Seats are not comfortable and in flight entertainment was not working.
Search United Airlines flights
American AirlinesPriceFrom $127First ClassRating
7.2
See reviews
7.5

Boarding

7.2

Comfort

8.0

Crew

6.9

Entertainment

6.4

Food

Reviews

1 / 10
People people need to wait for their time to board and not line up in the walkway of the terminal. You would think with air travel being a few years old would find an efficient and less stressful way to board planes.
Search American Airlines flights
Spirit AirlinesPriceFrom $48First ClassRating
6.3
See reviews
6.6

Boarding

5.9

Comfort

7.0

Crew

4.9

Entertainment

5.1

Food

Reviews

1 / 10
It was ok
Search Spirit Airlines flights

    About Business Class Flights to Chicago

    Helpful overview information on Chicago Business Class ticket prices, flight duration, and airlines

    Fastest flight time

    		0h 50m

    Closest Airport

    		Milwaukee-Mitchell

    Most Popular Airline

    		Delta
    The quickest Business Class flight you can catch to Chicago takes 0h 50m, which departs from Milwaukee-Mitchell to Chicago Midway.
    The nearest airport for all arrivals to Chicago is Milwaukee-Mitchell. Business Class flyers can expect to travel 66.8 mi to get to downtown.
    The most popular airline for Business Class flights to Chicago found on momondo this week is Delta, with a user rating of 7.9/10. There are 4 airlines in total servicing this route with Business Class options.
    Search flight deals

    Frequently asked questions about Chicago Business Class flights

    Is it worth flying Business Class to Chicago?

    Many flyers choose booking Business Class tickets to Chicago because of the many premium services/perks they may come with, such as extra legroom, lounge access, in-flight dining, entertainment, and more. Different airlines will have their own unique offerings for this premium cabin, so you may have to check with airlines’ websites just to be sure. In the meantime, momondo can help you find cheap deals for Business Class flights available on the web.

    Why should I use momondo to find a Business Class flight deal to Chicago?

    momondo collates all your flight options in one place and lets you filter them to find the perfect Business Class flight to Chicago. momondo saves you time and could save you money on your trip.

    Can I find Business Class flights to Chicago with flexible booking policies on momondo?

    Business Class flights to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

    How can momondo help me find deals for Business Class flight tickets to Chicago?

    Once you have performed a search for Business Class flight tickets to Chicago, momondo helps you find the right flight by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

    I’m not ready to book a Business Class flight to Chicago right now. Can momondo alert me if prices change?

    Price alerts on Business Class flights to Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

    When did momondo last update prices for flights from United States to Chicago?

    Prices for flights from United States to Chicago are updated daily.

    How many operators does momondo search for flights from United States to Chicago?

    The number of operators available for flights from United States to Chicago is 11 as of February 2026.

    How old do you have to be to fly from United States to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from United States to Chicago.

    What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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    Find better results for your trip to Chicago

    Airports near Chicago

    Airports listed have a maximum distance of 79.0 mi from Chicago
    Flights to Chicago Midway Airport
    Flights to Chicago O'Hare Intl Airport
    Flights to Chicago Greater Rockford Airport