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Find First Class Flights to Chicago

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Flights Deals

Cheap First Class Flight Deals to Chicago

 
These are the cheapest deals for flights from the United States to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent first class round-trip flight deals to Chicago

Mon, Aug 11 - Wed, Aug 13
United Airlines Logo
5:00 pm - 6:16 pmDCA-ORD
2h 16mnonstop
United Airlines Logo
8:00 am - 10:56 amORD-DCA
1h 56mnonstop
$363United Airlines
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Tue, Sep 2 - Fri, Sep 5
United Airlines Logo
6:10 am - 8:05 amBOS-ORD
2h 55mnonstop
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
$368United Airlines
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Wed, Jul 23 - Wed, Jul 30
American Airlines Logo
7:00 am - 9:05 amBOS-ORD
3h 05mnonstop
American Airlines Logo
6:25 am - 9:49 amORD-BOS
2h 24mnonstop
$369American Airlines
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Sat, Oct 18 - Wed, Oct 22
American Airlines Logo
7:41 pm - 9:25 pmEWR-ORD
2h 44mnonstop
American Airlines Logo
7:04 am - 10:20 amORD-EWR
2h 16mnonstop
$379American Airlines
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Wed, Sep 3 - Fri, Sep 5
Delta Logo
8:00 am - 9:55 amJFK-ORD
2h 55mnonstop
Delta Logo
7:00 am - 10:23 amORD-JFK
2h 23mnonstop
$457Delta
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Wed, Sep 10 - Wed, Sep 17
Delta Logo
1:00 pm - 6:37 pmEWR-MDW
6h 37m1 stop
Delta Logo
1:08 pm - 7:24 pmMDW-EWR
5h 16m1 stop
$507Delta
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Fri, Sep 19 - Mon, Sep 22
Alaska Airlines Logo
5:14 pm - 7:03 amSFO-ORD
11h 49m2 stops
Alaska Airlines Logo
8:00 am - 3:52 pmORD-SFO
9h 52m1 stop
$847Alaska Airlines
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Sun, Sep 28 - Mon, Oct 6
Hawaiian Airlines Logo
9:19 pm - 7:03 amSFO-ORD
7h 44m1 stop
Hawaiian Airlines Logo
8:20 am - 2:01 pmORD-SFO
7h 41m1 stop
$876Hawaiian Airlines
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Thu, Sep 25 - Sun, Sep 28
Hawaiian Airlines Logo
6:45 pm - 5:00 amSFO-ORD
8h 15m1 stop
Hawaiian Airlines Logo
7:00 am - 12:30 pmORD-SFO
7h 30m1 stop
$896Hawaiian Airlines
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Fri, Sep 12 - Mon, Sep 15
Alaska Airlines Logo
5:14 pm - 7:03 amSFO-ORD
11h 49m2 stops
Alaska Airlines Logo
1:01 pm - 7:19 pmORD-SFO
8h 18m1 stop
$897Alaska Airlines
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Good to Know - First Class Flights to Chicago

Low seasonFebruary
High seasonSeptember
Average price round-trip$2,266
Good deal round-trip$517
Good deal one-way$355
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 9% lower on average.
(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
To calculate monthly average prices, KAYAK takes all prices for each month over the last year for first class flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all the values for each month.
Flight prices as travel date approaches
To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for first class flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.

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.

  • How long is a flight to Chicago?

    Flights from Dallas2h 33m
    Flights from New York2h 27m
    Flights from Denver2h 40m
    Flights from Boston2h 37m
    Flights from Miami3h 19m
  • 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 Hawaiian Airlines.

  • 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.
  • The most expensive day to fly First Class to Chicago is Saturday, while the cheapest is Thursday.

Reviews of the top 5 airlines flying to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from the United States to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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
Alaska AirlinesOverall score based on 10000 reviews
8.1Boarding
8.5Crew
7.1Entertainment
7.8Comfort
7.1Food
Airline reviews

fine. only problem,,,, for some,,,,was that many people started trying to exit from the back of the plane,, . lots of irate people. there should be a flight attendant mid plane..to be sure that doesn't happen. The crew up front had no idea what was happening. One big guy started it..then a bunch of others followed his lead. could have gotten ugly... One man stepped in and questioned those rule breakers.. nothing bad happened,,,but......

8.0 ExcellentLiz, Jul 2025SFO - SEA
Read more Alaska Airlines reviews

fine. only problem,,,, for some,,,,was that many people started trying to exit from the back of the plane,, . lots of irate people. there should be a flight attendant mid plane..to be sure that doesn't happen. The crew up front had no idea what was happening. One big guy started it..then a bunch of others followed his lead. could have gotten ugly... One man stepped in and questioned those rule breakers.. nothing bad happened,,,but......

It was fine. 2 hour delay due to mechanical issue. I understand issues will occur, just wish instead of Capt repeatedly telling us we will be getting off the ground “momentarily” they would just be honest and either say they have no idea-or it’s going to be a few hours! All in all FAs are usually pretty nice :)

Big delay of over 7 hours on next leg of trip with Alaska. Would have been nice to have food or something

We were late so that was what was worst part

Flying on Hawaiian Airlines was good. But, getting a boarding pass was a hassle. I booked what I thought was an Alaska Airlines flight that was actually a Hawaiian Airlines flight. I couldn't check in online. I had to wait for the Hawaiian Airlines counter to open so I could get my boarding pass which was a requirement for me to get in The Club or the Centurion Lounge. (I had no check in luggage so I didn't expect to have to physically check in.) The Alaska Airlines staff blamed the FAA for the problem.

Way too warm for that length of flight!! If the pretzel bag gets any smaller, there won't even be any pretzels to eat!! Crew didn't talk. $99 just for an aisle seat is ludicrous!! Probably won't fly Alaska again.

Great, overall. Thicker seat cushion would be nice. My butt hurt the whole flight.

All good! No entertainment on this new plane yet but ok for this short flight. Great on time flight! Thanks

No non-alcoholic drinks available except water and small apple juice cans.

The flight was delayed over two and a half hours thus causing me to miss my best friend’s funeral. All because the flight crew had to get more rest. That was the reason stated. I understand however very unfortunate. Glad everyone is well rested and resting in peace.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

Overall it was a good flight, but the food should be looked at. No options. The seat was also uncomfortable and very tight.

I was unable to get a check im and get a boarding pass. I tried at the desk of the flight operator Alaska, was told to go to Hawaiian and almost had to go back to Alaskan. In the end inwas told to go thru security and directly to the gate without checking in. It would have been more helpful to have the details rather than walking all over the terminals trying to check in.

The middle name gave us so much issue at check in we had done middle names when booking but Hawaiian/Alaska don’t recognize the middle names and gave us problems at check in. We have never experienced that before.

I was booked thru Hawaiian Airlines (HA) on Kayak in February. I got 2 confirmation emails from Hawaiian Airlines in February. Even though the flight ticket informed me the flight was marketed thru HA and operated by Alaska Airlines (AA), I was never given any confirmation codes or anything from Kayak or AA to check into my flight online ahead of time. They also couldn't find the HA flight number I was given on their website and was told my flight did not exist unless I searched thru the AA website for flight details that was similar to the info HA gave me. The only way to check into my flight and make sure the flight still existed required me to get there 4 hours early. When I arrived at the airport, HA desk told me to go to AA desk. First AA desk redirected me to another desk, second AA desk told me to find someone with an iPad, and finally the iPad rep was able to help me. I also had to chat with AA reps online the night previous to my return trip because the same issue occurred.

I did not board neither one of my flights because It got delayed and I had to be at my destination at a certain time

We were delayed at the SD gate for close to an hour before we were allowed to depart for SJ. Reason given was inadequate ground crew to move the plane from the gate.

Thanks to the supervisor Jose my pregnant wife and our family will not miss a very important ultrasound tomorrow. What he did was simply heroic. He needs to be promoted and praised. Please tell him our family appreciates him so so much!

Your crew shortage delayed departure by an hour resulting in us missing an event we had scheduled for that afternoon outside of Fresno.

Check in process was a mess. Long lines, equipment malfuctioning. One line for baggage tags then a second line for bag checkin.

Both flights were late 2+ hours with ZERO communication from the airlines or their staff. No offers for compensation. WiFi didn’t work for streaming and they said to only use browsing but that didn’t work either. Waste of $$. No drinks only boxed water or apple juice. No snack. One of the worst flight experiences I’ve ever had.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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