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Cheap First Class Flight Deals to Chicago

 
Thu, Dec 3 - Sat, Dec 5
Delta Logo
8:59 pm - 10:57 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 58mnonstop
Delta Logo
7:05 am - 10:36 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 31mnonstop
$393Delta
Tue, Nov 10 - Wed, Nov 11
Delta Logo
8:30 pm - 10:18 pmLGA  New York LaGuardia-ORD Chicago O'Hare Intl
2h 48mnonstop
Delta Logo
2:37 pm - 5:47 pmORD  Chicago O'Hare Intl-LGA New York LaGuardia
2h 10mnonstop
$413Delta
Fri, Nov 20 - Sun, Nov 22
Delta Logo
8:40 pm - 10:36 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 56mnonstop
Delta Logo
7:05 am - 10:32 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 27mnonstop
$457Delta
Thu, Dec 10 - Thu, Dec 17
American Airlines Logo
7:22 pm - 8:49 pmATL  Atlanta Hartsfield-Jackson-ORD Chicago O'Hare Intl
2h 27mnonstop
American Airlines Logo
4:29 pm - 7:41 pmORD  Chicago O'Hare Intl-ATL Atlanta Hartsfield-Jackson
2h 12mnonstop
$500American Airlines
Sat, Nov 7 - Sat, Nov 7
American Airlines Logo
7:14 am - 9:30 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 16mnonstop
American Airlines Logo
1:37 pm - 5:08 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 31mnonstop
$501American Airlines
Thu, Dec 10 - Sat, Dec 12
American Airlines Logo
9:25 pm - 11:00 pmPHL  Philadelphia-ORD Chicago O'Hare Intl
2h 35mnonstop
American Airlines Logo
6:00 am - 9:11 amORD  Chicago O'Hare Intl-PHL Philadelphia
2h 11mnonstop
$504American Airlines
Sat, Nov 7 - Sat, Nov 7
United Airlines Logo
6:00 am - 8:00 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 00mnonstop
United Airlines Logo
3:35 pm - 9:59 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
5h 24m1 stop Newark
$531United Airlines
Wed, Nov 11 - Sat, Nov 14
United Airlines Logo
6:00 am - 1:04 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
8h 04m2 stops Newark Cleveland Hopkins Intl
United Airlines Logo
7:00 am - 12:26 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
4h 26m1 stop Newark
$546United Airlines
Fri, Mar 5 - Fri, Mar 12
Alaska Airlines Logo
9:59 pm - 1:54 pmSFO  San Francisco-ORD Chicago O'Hare Intl
13h 55m1 stop San Diego
Alaska Airlines Logo
2:54 pm - 7:40 pmORD  Chicago O'Hare Intl-SFO San Francisco
6h 46m1 stop San Diego
$917Alaska Airlines
Sat, Dec 26 - Sat, Jan 2
Alaska Airlines Logo
11:39 pm - 5:40 amSEA  Seattle/Tacoma Intl-ORD Chicago O'Hare Intl
4h 01mnonstop
Alaska Airlines Logo
6:00 am - 9:00 amORD  Chicago O'Hare Intl-SEA Seattle/Tacoma Intl
5h 00mnonstop
$957Alaska Airlines

Good to Know - First Class Flights to Chicago

Low season

December

Average price round-trip

$1,301

Good deal round-trip

$1,106

Good deal one-way

$454
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 1% 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 7.9.

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 $513 or less one-way and $935 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.
7.9
SouthwestOverall score based on 4210 reviews
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

The entire crew were wonderful but 1 flight attendant stood out with his sense of humor on the microphone. I told him as much as I exited the plane.

8.0 ExcellentDanielle, Oct 2026
Read more Southwest reviews

The entire crew were wonderful but 1 flight attendant stood out with his sense of humor on the microphone. I told him as much as I exited the plane.

Maybe different snack selection. To much sodium in them. I know refrigerators are not available but there has to be healthier items.

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

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.

Requested an aisle seat at the gate and got it. The staff so friendly

Flight was very delayed so I was able to get on an earlier flight via stand-by. Crew communicated effectively around delay and worked to make customers comfortable. Wifi was ok, streaming TV was great. App functionality broke down once I was moved to stand-by on earlier flight.

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

Requested for warm or hot water because of throat pain, it was denied. The entertainment system was hung, requested the crew to turn it off, instead of turning it off they rebooted the device. It was stuck again, no one bothered to check.

Horrible on the chicago end. They change hates then there is a plane at the new gate so we can’t pull in. Then that plane has mechanical issue and needs to be pulled back to the gate but we can’t get to another new gate due the other plane being in the way. Horrible gate management which will cause many customers to miss connections.

Fantastic experience once again flying with United! There was great communication from the cockpit and one of the flight attendants went out of her way to get my two little kids some special treats which elevated our travel experience coming home.

Flights was great, service and transit support was outstanding - but the food was limited and of poor quality - only a snack on the first hour for 2 hours 1/2 leg. and a light breakfast on the second 4 hour leg.

The employees seemed impatient with their guests. It seemed like they were giving us orders, instead of easily assisting. Our flight was delayed waiting on a flight attendant. It was alright.

My easiest trip ever. Flights left on time, and came in a few minutes early. The flights weren’t full so it was very comfortable. Thank you United

Quinoa chocolate cookies are my favorite! Would be nice to have internet service like American

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.

Same the delay was not ideal and the credits to move flights was not sufficient

No food on 4.5 hour flight, wi-fi did not work. Terrible experience for a long haul flight.

The crew were diligent about ensuring that our pet dog remained in his carrier for the entire flight, as is their mandate. I wish that mandate was changed so that our poor, scared pets can be comforted during a flight, whereas service animals get to stay out and about for the whole flight. Thank you.

first leg from san diego to chicago, only had cookies for snack. 1 flavor of sparkling water chicago to washington dc had option of cookies, pretzels, or gold fish. had 2 flavors of sparkling water. 2nd flight better however the best part was there was no delays!!! Got to chicago and washington dc early. That was wonderful!!!!

Business class flight attendant was very good. But our flight was delayed two hours for a “mechanical” bathroom issue that literally took 5 minutes to fix. Our plane landed early from its previous flight but still waited for a mechanic to show up to fix an obvious minor issue for almost three hours. This caused us to miss our connecting flight. They put us up in a Days Inn that was 17 miles away from the airport that took a half hour of driving just to get to and this was at 11pm at night. Then when we finally got back on a plane after a full day delay they left our luggage back in the airport. This was an international flight, so no luggage or belongings after flying 8 hours to a different country. We will NEVER fly American Airlines again.

12 hour wait in pdx to my initial flight to Dallas to hunstville

The flight from Chicago to Orlando was delayed inordinately. My whole journey from Lansing to MCO took 9.5 hours is just annoying and frustrating. We can understand the delays may be beyond their control, but overall the journey was so much waiting until reached to MCO. This is NOT the first time for me - but at least 80% of the time in this route. I barely remember reaching places on time.

I was truly shocked at how poor this flight went. The crew was not friendly during the checking process. The asked for people to gate check and were rude about it. They didn't handle my luggage with care. When I got to my seat I noticed a large section of the ceiling vent area was, no joke, TAPED TOGETHER WITH CLEAR PACKING TAPE! To add insult to injury, the back rest button was disabled on my seat and all the seats I could see. The wifi, never connected for me, despite troubleshooting it for a while. I did everything from restarting my wifi/phone to forgetting the network and restarting the app. But that didn't stop the mandatory 2 ads from playing every single time. Even the bags took over 45 mins to arrive at the carousel. Everything about this flight was a flop and I am beginning to notice that some of these events are becoming a trend. Perhaps it's time I switch loyalty programs.

It would be helpful to be able to download an eticket from either American airlines or Cathay Pacific; not just Cathay Pacific.

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.

More options for your flight to Chicago

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