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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.
Spirit Airlines Logo
10:54 pm - 12:22 am
EWR
-
ORD
2h 28mnonstop
Spirit Airlines Logo
12:47 pm - 3:54 pm
ORD
-
EWR
2h 07mnonstop
$190Spirit Airlines
Mon, Apr 13 - Thu, Apr 16
Spirit Airlines Logo
10:54 pm - 12:22 am
EWR
-
ORD
2h 28mnonstop
Spirit Airlines Logo
11:28 am - 5:34 pm
ORD
-
EWR
5h 06m
1 stop
$209Spirit Airlines
Mon, Apr 13 - Thu, Apr 16
American Airlines Logo
6:19 am - 9:55 am
DEN
-
ORD
2h 36mnonstop
American Airlines Logo
10:19 pm - 12:06 am
ORD
-
DEN
2h 47mnonstop
$372American Airlines
Sat, May 16 - Wed, May 20
American Airlines Logo
6:55 am - 10:33 am
DEN
-
ORD
2h 38mnonstop
American Airlines Logo
10:19 pm - 11:59 pm
ORD
-
DEN
2h 40mnonstop
$373American Airlines
Sat, Jun 13 - Wed, Jun 17
Delta Logo
10:24 am - 12:26 pm
JFK
-
ORD
3h 02mnonstop
Delta Logo
6:04 am - 9:29 am
ORD
-
JFK
2h 25mnonstop
$419Delta
Tue, Apr 28 - Thu, Apr 30
Delta Logo
7:36 pm - 9:57 pm
JFK
-
ORD
3h 21mnonstop
Delta Logo
6:04 am - 9:29 am
ORD
-
JFK
2h 25mnonstop
$427Delta
Wed, Apr 29 - Thu, Apr 30
United Airlines Logo
12:26 pm - 2:55 pm
DFW
-
ORD
2h 29mnonstop
United Airlines Logo
8:00 pm - 10:53 pm
ORD
-
DFW
2h 53mnonstop
$432United Airlines
Tue, May 5 - Fri, May 8
United Airlines Logo
12:26 pm - 2:55 pm
DFW
-
ORD
2h 29mnonstop
United Airlines Logo
12:40 pm - 6:30 pm
ORD
-
DFW
5h 50m
1 stop
$447United Airlines
Tue, May 5 - Tue, May 12
Alaska Airlines Logo
6:35 am - 6:40 pm
SFO
-
ORD
10h 05m
1 stop
Alaska Airlines Logo
3:52 pm - 11:01 pm
ORD
-
SFO
9h 09m
1 stop
$747Alaska Airlines
Tue, Apr 21 - Thu, May 7
Alaska Airlines Logo
9:15 pm - 6:40 am
SFO
-
ORD
7h 25m
1 stop
Alaska Airlines Logo
3:52 pm - 11:01 pm
ORD
-
SFO
9h 09m
1 stop
$769Alaska Airlines
Mon, Apr 27 - Thu, Apr 30

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?

Spirit Airlines, 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?

In general, June is the cheapest month to fly First Class from United States to Chicago. Due to it being the ‘off-season’ during this time, you can expect First Class flight prices to be around $1,097. If you aren’t able to travel during the month of June, then book First Class flights to Chicago from United States during November instead. First Class flights to Chicago in November, while not as cheap as those in June, still average around $1,107.

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 Saturday when prices can be found for as low as $470. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average First Class ticket price to Chicago on a Thursday is $959.

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 51m 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 March 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 41% of daily flights taking off at noon.

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

As of March 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 18% 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 $1,152/pp. Prices depend on where you are departing from. For prices as low as $393/pp, depart from Los Angeles. The most expensive round trip First Class flights to Chicago are from Los Angeles.

See prices from:

What airlines fly First Class to Chicago?

United Airlines is the most popular airline offering First Class flights to Chicago, with 45% 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
Alaska AirlinesPriceFrom $186First ClassRating
8.0
See reviews
8.1

Boarding

7.8

Comfort

8.5

Crew

7.0

Entertainment

7.1

Food

Reviews

1 / 10
The Alaska App doesn't always work properly.
Search Alaska Airlines flights
DeltaPriceFrom $78First 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
7.1
See reviews
7.5

Boarding

7.2

Comfort

7.9

Crew

6.9

Entertainment

6.4

Food

Reviews

1 / 10
This was by far the most disappointing airline experience I have had. My flight was canceled the day prior to departure, and I was informed the reason was weather-related. While I understand that weather can impact travel schedules, the issues continued the following day. Nearly every flight was delayed, with arriving aircraft coming in late and flight crews not being present at the gates on time. As a result, passengers were forced to rush to their connecting gates in order to avoid missing their next flights. Unfortunately, this appears to be an ongoing issue with American Airlines. The aircraft itself was also in poor condition; it had clearly not been properly cleaned prior to boarding. It was explained that there was no time to service the plane before passengers boarded again, which is concerning from both a comfort and professionalism standpoint. This level of service is unacceptable, especially considering the high cost of airfare. Passengers should not have to deal with canceled flights, repeated delays, or the stress of rushing between connections when itineraries were originally scheduled with sufficient travel time. As a Sailor who was home visiting family, the delays resulted in the loss of an entire day that could have been spent with them. I hope American Airlines takes these concerns seriously and works to improve scheduling, communication, and overall passenger experience.If you’d like, I can also make a shorter version for a complaint form or social media review that still sounds professional but hits harder.
Search American Airlines flights
Spirit AirlinesPriceFrom $46First ClassRating
6.3
See reviews
6.6

Boarding

5.9

Comfort

7.0

Crew

4.9

Entertainment

5.0

Food

Reviews

1 / 10
Flight was on time. Landing was great and on time. Boarding process was great and smooth
Search Spirit Airlines flights

    About First Class Flights to Chicago

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

    Fastest flight time

    		0h 50m

    Closest Airport

    		Milwaukee-Mitchell

    Most Popular Airline

    		Alaska Airlines
    The quickest First 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. First Class flyers can expect to travel 66.8 mi to get to downtown.
    The most popular airline for First Class flights to Chicago found on momondo this week is Alaska Airlines, with a user rating of 8.0/10. There are 5 airlines in total servicing this route with First Class options.
    Search flight deals

    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 10 as of March 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