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Business Class Flights to Chicago in 2025

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Cheap Business Class Flight Deals to Chicago

Recent business class round-trip flight deals to Chicago

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American Airlines Logo
7:29 pm - 8:57 pmBWI-ORD
2h 28mnonstop
American Airlines Logo
8:20 am - 11:22 amORD-BWI
2h 02mnonstop
$463American Airlines
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Mon, Dec 8 - Thu, Dec 11
American Airlines Logo
1:18 pm - 2:43 pmDCA-ORD
2h 25mnonstop
American Airlines Logo
12:59 pm - 3:59 pmORD-DCA
2h 00mnonstop
$465American Airlines
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Mon, Dec 8 - Thu, Dec 11
American Airlines Logo
7:29 pm - 8:57 pmBWI-ORD
2h 28mnonstop
American Airlines Logo
6:35 pm - 12:23 amORD-BWI
4h 48m1 stop
$473American Airlines
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Mon, Dec 8 - Thu, Dec 11
American Airlines Logo
6:33 pm - 10:28 pmDCA-ORD
4h 55m1 stop
American Airlines Logo
12:59 pm - 3:59 pmORD-DCA
2h 00mnonstop
$475American Airlines
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Mon, Dec 8 - Thu, Dec 11
American Airlines Logo
3:55 pm - 7:03 pmDCA-ORD
4h 08m1 stop
American Airlines Logo
3:30 pm - 8:59 pmORD-DCA
4h 29m1 stop
$484American Airlines
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Mon, Dec 8 - Thu, Dec 11
American Airlines Logo
11:25 am - 3:09 pmIAD-ORD
4h 44m1 stop
American Airlines Logo
7:10 am - 1:20 pmORD-IAD
5h 10m1 stop
$484American Airlines
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Mon, Dec 8 - Thu, Dec 11
American Airlines Logo
8:29 pm - 10:33 pmLGA-ORD
3h 04mnonstop
American Airlines Logo
7:30 am - 1:56 pmORD-LGA
5h 26m1 stop
$522American Airlines
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Tue, Nov 11 - Thu, Nov 13
American Airlines Logo
12:44 pm - 7:20 pmLGA-ORD
7h 36m1 stop
American Airlines Logo
6:06 am - 11:29 amORD-LGA
4h 23m1 stop
$569American Airlines
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Tue, Nov 11 - Thu, Nov 13
Alaska Airlines Logo
5:50 pm - 11:59 pmSEA-ORD
4h 09mnonstop
Alaska Airlines Logo
6:00 am - 8:45 amORD-SEA
4h 45mnonstop
$847Alaska Airlines
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Sun, Dec 7 - Tue, Dec 30
Alaska Airlines Logo
2:08 pm - 11:50 pmSEA-ORD
7h 42m1 stop
Alaska Airlines Logo
6:00 am - 8:45 amORD-SEA
4h 45mnonstop
$867Alaska Airlines
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Tue, Dec 9 - Mon, Dec 29

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 $449. If you aren’t able to travel during the month of January, then book Business Class flights to Chicago from United States during February instead. Business Class flights to Chicago in February, while not as cheap as those in January, still average around $500.

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 Saturday when prices can be found for as low as $350. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average Business Class ticket price to Chicago on a Monday is $1,817.

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 45m on average, while flying from Boston to Chicago O'Hare Intl Airport is 2h 50m 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 October 2025, 227 flights take off from United States and land in Chicago each day. The most common flight departure time for this route is 11:00AM, with 43% of daily flights taking off at noon.

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

As of October 2025, 1,589 flights take off from United States and land in Chicago each week. The most common flight departure day for this route is Thu, with 36% 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 $1,388/pp. Prices depend on where you are departing from. For prices as low as $686/pp, depart from New York. The most expensive round trip Business Class flights to Chicago are from San Francisco.
See prices from:

What airlines fly Business Class to Chicago?

United Airlines is the most popular airline offering Business Class flights to Chicago, with 59% 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
Alaska AirlinesPriceFrom $196First ClassRating
8.0
8.1

Boarding

7.8

Comfort

8.5

Crew

7.0

Entertainment

7.1

Food

Reviews

1 / 10
I can’t imagine that it took 9 hours to fly from DC to LA even it’s a direct fly only because of the plane maitainent problem
Search Alaska Airlines flights
DeltaPriceFrom $101First ClassRating
7.9
8.2

Boarding

7.9

Comfort

8.5

Crew

7.9

Entertainment

7.3

Food

Reviews

1 / 10
Excellent
Search Delta flights
United AirlinesPriceFrom $129First ClassRating
7.4
7.7

Boarding

7.3

Comfort

8.1

Crew

7.1

Entertainment

6.6

Food

Reviews

1 / 10
Mostly friendly employees, choice of snacks and beverages. Although on one of the flights there was only one snack left out of three.
Search United Airlines flights
American AirlinesPriceFrom $136First ClassRating
7.2
7.5

Boarding

7.2

Comfort

8.0

Crew

6.9

Entertainment

6.4

Food

Reviews

1 / 10
The flight attendant was particularly nice to me. Charging for advance seat assignments is a ridiculous way to increase revenue. Just raise the ticket price. Silly.
Search American Airlines flights

    About Business Class Flights to Chicago

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

    Fastest flight time

    		2h 24m

    Closest Airport

    		Chicago O'Hare Intl

    Most Popular Airline

    		Alaska Airlines
    The quickest Business Class flight you can catch to Chicago takes 2h 24m, which departs from Dallas/Fort Worth to Chicago O'Hare Intl.
    The nearest airport for all arrivals to Chicago is Chicago O'Hare Intl. Business Class flyers can expect to travel 15.9 mi to get to downtown.
    The most popular airline for Business Class flights to Chicago found on momondo this week is Alaska Airlines, with a user rating of 8.0/10. There are 4 airlines in total servicing this route with Business Class options.
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    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.

    How long does it take to fly to Chicago?

    While the flight duration may vary for Business Class travelers depending on the departure and arrival airports, here are some average flight times from popular locations you might be interested in:

    Baltimore to Chicago: 2 hours 5 minutes
    Tampa to Chicago: 2 hours 57 minutes
    West Palm Beach to Chicago: 3 hours 17 minutes
    Miami to Chicago: 3 hours 18 minutes
    New York to Chicago: 2 hours 29 minutes
    Dallas/Fort Worth Airport to Chicago: 2 hours 37 minutes
    Denver to Chicago: 2 hours 39 minutes

    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 October 2025.

    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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    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