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First Class Flights to Chicago in 2026

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Cheap First Class Flight Deals to Chicago

Recent first class round-trip flight deals to Chicago

Enter your travel dates to find the best prices.
Delta Logo
7:30 am - 9:27 amJFK  New York John F Kennedy Intl-ORD Chicago O'Hare Intl
2h 57mnonstop
Delta Logo
6:10 am - 9:27 amORD  Chicago O'Hare Intl-JFK New York John F Kennedy Intl
2h 17mnonstop
$385Delta
Tue, Oct 20 - Thu, Oct 22
Delta Logo
7:35 pm - 9:43 pmJFK  New York John F Kennedy Intl-ORD Chicago O'Hare Intl
3h 08mnonstop
Delta Logo
6:00 am - 9:24 amORD  Chicago O'Hare Intl-JFK New York John F Kennedy Intl
2h 24mnonstop
$403Delta
Sat, Nov 7 - Sat, Nov 14
Delta Logo
7:30 am - 9:27 amJFK  New York John F Kennedy Intl-ORD Chicago O'Hare Intl
2h 57mnonstop
Delta Logo
6:00 am - 9:20 amORD  Chicago O'Hare Intl-JFK New York John F Kennedy Intl
2h 20mnonstop
$403Delta
Wed, Oct 14 - Tue, Feb 23
American Airlines Logo
7:23 pm - 9:29 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 06mnonstop
American Airlines Logo
7:00 am - 10:33 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 33mnonstop
$425American Airlines
Wed, Oct 14 - Sun, Oct 18
American Airlines Logo
7:00 am - 9:05 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 05mnonstop
American Airlines Logo
6:00 am - 9:37 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 37mnonstop
$425American Airlines
Wed, Oct 21 - Sun, Oct 25
American Airlines Logo
7:14 am - 9:30 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 16mnonstop
American Airlines Logo
8:00 pm - 11:31 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 31mnonstop
$425American Airlines
Fri, Nov 6 - Mon, Nov 9
United Airlines Logo
7:01 am - 9:00 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 59mnonstop
United Airlines Logo
6:10 am - 9:33 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 23mnonstop
$489United Airlines
Wed, Oct 21 - Sat, Oct 24
United Airlines Logo
4:29 pm - 6:36 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 07mnonstop
United Airlines Logo
6:50 am - 10:17 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 27mnonstop
$489United Airlines
Fri, Dec 25 - Tue, Dec 29
Alaska Airlines Logo
6:00 am - 6:55 pmSFO  San Francisco-ORD Chicago O'Hare Intl
10h 55m1 stop San Diego
Alaska Airlines Logo
7:55 pm - 8:02 amORD  Chicago O'Hare Intl-SFO San Francisco
14h 07m1 stop San Diego
$824Alaska Airlines
Fri, Feb 26 - Wed, Mar 3
Alaska Airlines Logo
7:21 am - 10:08 pmSFO  San Francisco-ORD Chicago O'Hare Intl
12h 47m2 stops Las Vegas Harry Reid Intl San Diego
Alaska Airlines Logo
3:09 pm - 11:59 pmORD  Chicago O'Hare Intl-SFO San Francisco
10h 50m1 stop Seattle/Tacoma Intl
$905Alaska Airlines
Wed, Feb 10 - Tue, Feb 16

First Class Flights to Chicago - Travel Insights & Trends

Get data-powered insights and trends for First 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 First Class from United States to Chicago?

Delta, American Airlines, and United Airlines are popular carriers operating the cheapest First Class flights from United States to Chicago

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

The month of February is, on average, the cheapest month to fly First Class to Chicago, with most prices found around $709. If you aren’t able to travel during the month of February, then book flights to Chicago during November instead. Flights to Chicago in November, while not as cheap as those in February, still average around $750.

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

The cheapest day to depart from United States to Chicago is on a Tuesday when prices can be found for as low as $755. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average First Class ticket price to Chicago on a Monday is $1,598.

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 48m 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 September 2026, 491 flights take off from United States and land in Chicago each day. The most common flight departure time for this route is 10:00AM, with 38% of daily flights taking off at noon.

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

As of September 2026, 3,439 flights take off from United States and land in Chicago each week. The most common flight departure day for this route is Wed, with 20% of weekly flights taking off on this day.

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

On average, round trip First Class flights to Chicago cost $1,272/pp. Prices depend on where you are departing from. For prices as low as $408/pp, depart from Boston. The most expensive round trip First Class flights to Chicago are from Boston.

See prices from:

What airlines fly First Class to Chicago?

United Airlines is the most popular airline offering First Class flights to Chicago, with 46% 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 First Class Flights to Chicago

Book reliable First Class tickets to Chicago from top-rated airlines
AirlineRatingFirst ClassPrice
DeltaPriceFrom $366First ClassRating
7.8
See reviews
8.1

Boarding

7.8

Comfort

8.5

Crew

7.8

Entertainment

7.2

Food

Reviews

1 / 10
Gate agent released plane early. I missed the flight because the door closed 20 minutes before departure and did not reopen until the plane departed.
Search Delta flights
United AirlinesPriceFrom $218First ClassRating
7.4
See reviews
7.7

Boarding

7.3

Comfort

8.1

Crew

7.1

Entertainment

6.7

Food

Reviews

1 / 10
Smooth
Search United Airlines flights
American AirlinesPriceFrom $260First ClassRating
7.1
See reviews
7.4

Boarding

7.2

Comfort

7.9

Crew

6.8

Entertainment

6.4

Food

Reviews

1 / 10
Plane seats were too short. The head rest was against my shoulders pushing me forward and could not be adjusted. I’m only 6’ tall.
Search American Airlines flights

  • How much does a first class flight to Chicago cost?

    Depending on where you fly from and which dates you’d like to travel, the average price for a first class ticket to Chicago is approximately $1,082. If you fly from United States, you may be able to secure a first class seat at just $179 - price last found on Sep 12.

  • Which airlines have first class flights to Chicago?

    Flying with a first class ticket can make the travel experience more special. Popular airlines that have first class flights to Chicago include United Airlines, Delta, American Airlines, Spirit Airlines, Alaska Airlines. Please refer to individual airlines for details on premium services.

  • What is the cheapest business class flight to Chicago?

    Instead of flying first class, you can opt for a business class flight to Chicago for about 142% less. business class flights, on average, will cost $2,623 per person and provide flyers with similar great perks and comfort.

  • Which cabin class is available for United Airlines flights to Chicago?

    United Airlines, the most popular airline for flights to Chicago, has a cabin alternative to Economy seats: first class. For flyers that want more travel options, try looking at another airline or departing origin.

About First Class Flights to Chicago

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

Fastest flight time

1h 12m

Closest Airport

Milwaukee-Mitchell

Most Popular Airline

Delta
The quickest First Class flight you can catch to Chicago takes 1h 12m, which departs from Madison Truax Field to Chicago O'Hare Intl.
The nearest airport for all arrivals to Chicago is Milwaukee-Mitchell. First Class flyers can expect to travel 80.5 mi to get to downtown.
The most popular airline for First Class flights to Chicago found on momondo this week is Delta, with a user rating of 7.8/10. There are 3 airlines in total servicing this route with First Class options.
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Frequently asked questions about Chicago First Class flights

Is it worth flying First Class to Chicago?

Many flyers choose booking First 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 First Class flights available on the web.

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

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

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

First 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 First Class flight tickets to Chicago?

Once you have performed a search for First 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 First Class flight to Chicago right now. Can momondo alert me if prices change?

Price alerts on First 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 8 as of September 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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