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Find First Class Flights to Chicago

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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

Tue, Sep 16 - Thu, Sep 18
American Airlines Logo
11:23 am - 12:40 pmBWI-ORD
2h 17mnonstop
American Airlines Logo
7:54 am - 10:53 amORD-BWI
1h 59mnonstop
$343American Airlines
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Tue, Aug 19 - Sun, Aug 24
American Airlines Logo
12:22 pm - 1:40 pmBWI-ORD
2h 18mnonstop
American Airlines Logo
8:45 am - 11:52 amORD-BWI
2h 07mnonstop
$352American Airlines
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Thu, Nov 20 - Sun, Nov 23
United Airlines Logo
7:50 am - 9:50 amBOS-ORD
3h 00mnonstop
United Airlines Logo
6:15 am - 9:30 amORD-BOS
2h 15mnonstop
$407United Airlines
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Fri, Sep 12 - Sun, Sep 14
United Airlines Logo
6:16 pm - 8:10 pmBOS-ORD
2h 54mnonstop
United Airlines Logo
7:30 am - 11:01 amORD-BOS
2h 31mnonstop
$408United Airlines
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Sat, Aug 23 - Mon, Aug 25
Delta Logo
8:00 am - 9:55 amJFK-ORD
2h 55mnonstop
Delta Logo
7:00 am - 10:23 amORD-JFK
2h 23mnonstop
$491Delta
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Tue, Jul 29 - Wed, Jul 30
Delta Logo
8:00 am - 9:57 amJFK-ORD
2h 57mnonstop
Delta Logo
1:30 pm - 5:08 pmORD-JFK
2h 38mnonstop
$496Delta
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Tue, Sep 9 - Wed, Sep 17
Hawaiian Airlines Logo
12:59 am - 7:03 amSEA-ORD
4h 04mnonstop
Hawaiian Airlines Logo
8:00 am - 10:37 amORD-SEA
4h 37mnonstop
$759Hawaiian Airlines
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Mon, Aug 25 - Sun, Aug 31
Hawaiian Airlines Logo
12:59 am - 7:03 amSEA-ORD
4h 04mnonstop
Hawaiian Airlines Logo
2:07 pm - 8:35 pmORD-SEA
8h 28m1 stop
$803Hawaiian Airlines
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Tue, Sep 16 - Fri, Sep 19
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
$839Alaska Airlines
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Wed, Sep 17 - Tue, Sep 30
Alaska Airlines Logo
1:24 pm - 12:03 amSFO-ORD
8h 39m2 stops
Alaska Airlines Logo
8:00 am - 1:44 pmORD-SFO
7h 44m1 stop
$1,011Alaska Airlines
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Good to Know - First Class Flights to Chicago

Low seasonFebruary
High seasonAugust
Average price round-trip$2,404
Good deal round-trip$597
Good deal one-way$322
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 13% 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 26m
    Flights from Denver2h 40m
    Flights from Boston2h 37m
    Flights from Miami3h 16m
  • 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
7.1Food
7.8Comfort
7.1Entertainment
8.1Boarding
8.5Crew
Airline reviews

Wifi would be nice. Unfortunately the particular airplane was not equipped with wifi.

8.0 ExcellentAnonymous, Jul 2025SEA - ATL
Read more Alaska Airlines reviews

Wifi would be nice. Unfortunately the particular airplane was not equipped with wifi.

I'm so glad that Alaska still keeps this little "puddle-jumper" route going between SEA>ALW; my daughter lives on Walla Walla, and it's so much quicker to be able to fly right in to Walla Walla than to have to fly into Tri-Cities and then make her drive 40 minutes each way. This flight is usually only 50%-75% full when I fly it, but that's because it doesn't get in to ALW until MIDNIGHT! But thanks for continuing to service the Walla Walla area, Alaska!

Seats very comfortable and legroom appreciated. All in all, it was a great experience.

Original flight was canceled, and the automatically booked second flight was immediately delayed. I arrived about 4 hours later than planned with only a $12 meal voucher that didn't fully cover a sandwich at airport prices.

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......

I was expecting better service from Alaska Airlines. I registered for assistance since I have a disability. The terminal in Seattle, WA was very unprofessional and at times rude. The BWI location was the exact opposite. I will NOT consider Alaska Airlines for future flights.

It was very good and comfortable, Crew was also great

The flight was delayed almost an hour. No wifi on flight.

Good experience, although it was a little cramped being a tall person. Otherwise everything went smoothly and professionally though

Delay of more than 3 hours I didnt recieve neither a voucher for food Attention disaster

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.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

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.

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

Pre-Flight check-in Staff did a terrific job correcting a seat mis-assignment problem after I checked in the night before my flight. They really stepped up to make my flight home a joy. It was also my birthday, so the flight crew made me feel special a little treat.

Our flight delayed 2 hours, no WiFi in flight and the snack option isn’t great either.

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.

Nothing. Fare didn’t allow seat allocations. So we were stuck in the middle . Not good for 77 to 80 year olds. I was stick on plane. Taken off the plane before take off and ground staff told me to google where a hospital was to get a clearance to travel again. Left on own at airport ti fend for our selves. Also was charged for baggage, also I was not aware. I think booking through a third party, such as yourselves, doesn’t allow any for considerations when allocating seats.

I booked on Hawaiian and was bumped to an American airline flight in a different terminal. I was traveling with my two kids and told to take an air train to check my baggage in. We were given the last three seats in front of the toilet. Never flying Hawaiian again. Totally unreliable.

Good except that I couldn’t change seat and made me wait untill I checked 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.

Everything was great except for the delayed flight times (it was delayed twice).

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.

Traveling with my 90 year old mother, the boarding process was great, the gate crew was very helpful and friendly. One of the flight attendants was kind enough to assist her to and from the restroom mid-flight and cater to any requests she had. I wish I flew Hawaiian Airlines more often, it was a great trip!

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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