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Cheap First Class Flight Deals to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent first class round-trip flight deals to Chicago

Wed, Sep 23 - Thu, Sep 24
Delta Logo
7:35 am - 9:27 amJFK  New York John F Kennedy Intl-ORD Chicago O'Hare Intl
2h 52mnonstop
Delta Logo
6:00 am - 9:21 amORD  Chicago O'Hare Intl-JFK New York John F Kennedy Intl
2h 21mnonstop
$439Delta
Wed, Sep 30 - Fri, Oct 2
Delta Logo
7:35 am - 9:27 amJFK  New York John F Kennedy Intl-ORD Chicago O'Hare Intl
2h 52mnonstop
Delta Logo
6:00 pm - 9:43 pmORD  Chicago O'Hare Intl-JFK New York John F Kennedy Intl
2h 43mnonstop
$439Delta
Wed, Dec 16 - Fri, Dec 25
American Airlines Logo
7:14 am - 9:30 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 16mnonstop
American Airlines Logo
8:23 pm - 11:59 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 36mnonstop
$447American Airlines
Sat, Oct 3 - Sat, Oct 10
American Airlines Logo
6:00 am - 8:10 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 10mnonstop
American Airlines Logo
8:00 pm - 11:36 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 36mnonstop
$451American Airlines
Tue, Sep 22 - Fri, Sep 25
Delta Logo
7:35 pm - 9:37 pmJFK  New York John F Kennedy Intl-ORD Chicago O'Hare Intl
3h 02mnonstop
Delta Logo
6:00 pm - 9:43 pmORD  Chicago O'Hare Intl-JFK New York John F Kennedy Intl
2h 43mnonstop
$453Delta
Fri, Dec 25 - Tue, Dec 29
American Airlines Logo
7:38 am - 10:00 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 22mnonstop
American Airlines Logo
6:00 am - 9:35 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 35mnonstop
$460American Airlines
Tue, Oct 13 - Thu, Oct 15
United Airlines Logo
6:10 am - 7:25 amIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 15mnonstop
United Airlines Logo
12:55 pm - 4:01 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 06mnonstop
$588United Airlines
Wed, Nov 11 - Wed, Nov 11
United Airlines Logo
6:11 am - 7:30 amIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 19mnonstop
United Airlines Logo
9:41 pm - 12:30 amORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
1h 49mnonstop
$588United Airlines
Tue, Oct 27 - Sat, Oct 31
Alaska Airlines Logo
4:43 pm - 1:25 pmSFO  San Francisco-ORD Chicago O'Hare Intl
18h 42m1 stop San Diego
Alaska Airlines Logo
7:20 am - 12:41 pmORD  Chicago O'Hare Intl-SFO San Francisco
7h 21m1 stop San Diego
$850Alaska Airlines
Mon, Nov 16 - Fri, Nov 20
Alaska Airlines Logo
12:13 pm - 11:59 pmSFO  San Francisco-ORD Chicago O'Hare Intl
9h 46m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
7:57 pm - 8:52 amORD  Chicago O'Hare Intl-SFO San Francisco
14h 55m1 stop San Diego
$871Alaska Airlines

Good to Know - First Class Flights to Chicago

Low season

December

Average price round-trip

$1,530

Good deal round-trip

$1,301

Good deal one-way

$562
Best time to beat the crowds with an average 40% drop in price.
Most popular time to fly with an average 6% increase in price.
(avg. price over the last 2 weeks)
or less
or less

When to book first class flights to Chicago

Are your dates flexible? We break down the daily and monthly prices for first class flights to Chicago, so you can find the best time to fly.
Average price per month
Flight prices as travel date approaches

FAQs for Chicago first class flights

  • Which airline has the best first class amenities for flights to Chicago?

    If you reserve a first class flight to Chicago using American Airlines, you will have access to some of the world's best amenities. These range from their cozy, spacious, and luxurious seats to delicious meals and unlimited entertainment. First class passengers use seats with more legroom, ensuring their comfort the entire journey. Passengers are also served a variety of freshly prepared meals accompanied by drinks.

  • Which airline has the best flatbeds for first class flights to Chicago?

    American Airlines has the best flatbeds for first class flights to Chicago. The passengers are able to conveniently adjust their seats to a fully horizontal position. Their property of being spacious makes it possible for them to take any shape. Additionally, the process of adjusting the position of the seat is quite easy; the passenger is only required to press the adjust button, and everything is done.

  • Which airline has the best first class lounge amenities for flights to Chicago?

    The American Airlines' first class lounge has the best amenities. These include the spacious dining where passengers enjoy a variety of freshly prepared meals served with a rich selection of drinks. The lounge also has large flat-screen televisions that offer them unlimited entertainment as they wait for the plane.

  • What is the most popular airline offering First Class flights to Chicago?

    Among KAYAK users, American Airlines is the most popular airline offering First Class seats on flights to Chicago.

  • Which airlines offer First Class tickets on flights to Chicago?

    Traveling to Chicago and want to offer yourself a First Class experience? Depending on the origin, the following airlines offer seats in First Class: American Airlines, United Airlines, Alaska Airlines and Delta.

  • How does KAYAK find such good deals on First Class tickets to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago for economy class as well as First Class travelers.

  • What is the best airline for first class flights to Chicago?

    The highest-rated airline by KAYAK users offering first class flights to Chicago is Southwest, with an overall rating of 8.0.

Top tips for finding first class flights to Chicago

  • Booking first class flights to Chicago through the Chicago O' Hare International Airport and Chicago Midway International Airport will give you the advantage of a shorter security line. This will ensure that you do not waste time before getting to your luxurious seat.
  • Travelers at the Chicago O' Hare International Airport will be able to access the first class lounge at Terminal 3. Those at the Chicago Midway International Airport will be able to access the first-class lounge at Terminal 1.
  • Passengers using first class flights to Chicago will be the first to alight when their plane lands at Chicago O' Hare International Airport or Chicago Midway International Airport. Their luggage will also undergo security checks before that of the other passengers. This increases their level of convenience.
  • Try flying direct if you’re looking to save, as direct first class tickets are cheaper on average.
  • What’s a good price for a first class ticket between United States and Chicago? 25% of our users found flights on this route for $518 or less one-way and $887 or less round-trip.

Reviews of the top 5 airlines flying to Chicago

 
Need help choosing which airline to fly first class to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4195 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

Sat in the tarmac at O’Hare for 65 minutes. This is a regular occurrence for delta at O’Hare

Delta was fine though my flight was delayed 4 hours into LGA and my return into ORD involved a taxi of 1+ hour to the gate

It was as good as it could be. Flying is not a pleasant experience these days.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Smaller plane for a longer flight than my first one. Doesn’t make sense.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

The whole experience was excellent. As it most often is with Delta

Cabin was not pressurized properly. Several passengers had respiratory difficulties.

Very Very late. Subsequent flights left an hour before ours

Crew was great. Seats are cramped and uncomfortable and I’m a small person.

Awful. Delay after delay. And then again on the tarmac.

Kept changing the takeoff time and the moved it up so arrived when boarding had already started. Then sat waiting to taxi in for a long time

Food was not Good Nuts came very wet & not tasting Good Main course I asked for Steak they got me Chicken because they don’t have more !!!!

It cancelled and we were unable to catch our connecting international flights.

Leaving at 7 when scheduled to leave at 4:20 - you tell me. Understood there was a ground stop. Then having to "reboot" the plane because of a lighting strike, also understood. But basically the flight was a "clusterf#$%".

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

I had requested wheelchair assistance prior to flight. The airport staff had no record of it. It was not provided at Cedar Rapids which was a small airport, so I managed on my own. At O'Hare airport the same thing happened. The staff told me they had no record of my request for a wheel chair. But they finally provided it after a delay when I insisted that I needed it.

Our flight from Chicago to Des Moines was the problem flight due to a dismissive flight attendant. His conduct was unnecessary and unprofessional.. I will avoid using Americam Airlines again because of the situation. Very disappointing.

Mostly excellent. However, many too many gate changes. Connecting flight at ORD changed gate 6 times.

Mechanical issues and delays. I get it but bad experience. Turned my 3 hour airport experience into a 9 hours

The baggage process at the gate was terrible. Stay was not friendly at all

Flight was delayed because of mechanical. Could not get landing space which caused me to miss my connection. Messy and not organized.

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Little bit of trouble getting my KTN and pre-check status onto the ticket, but otherwise the counter staff were friendly and truly concerned to get it right.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

We were delayed three times ,and that destroyed my plans, and reservations

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

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