CHI

Find First Class Flights to Chicago

1 adult
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

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.

Recent first class round-trip flight deals to Chicago

Recommended first class round-trip deals departing in the coming months from the most popular airlines that fly to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
9:00 am - 11:01 amBOS-ORD
3h 01mnonstop
7:20 am - 10:42 amORD-BOS
2h 22mnonstop
$351American Airlines
Find Deal
Tue, Mar 4 - Thu, Mar 6
6:57 am - 10:51 amBOS-ORD
4h 54m1 stop
7:20 am - 10:42 amORD-BOS
2h 22mnonstop
$434American Airlines
Find Deal
Tue, Mar 4 - Thu, Mar 6
4:59 pm - 6:38 amEWR-ORD
14h 39m1 stop
10:53 am - 2:05 pmORD-EWR
2h 12mnonstop
$460United Airlines
Find Deal
Sat, Mar 8 - Sun, Mar 9
10:20 pm - 11:29 pmIAD-ORD
2h 09mnonstop
9:07 pm - 11:59 pmORD-IAD
1h 52mnonstop
$467United Airlines
Find Deal
Fri, Mar 7 - Mon, Mar 10
8:00 am - 9:52 amJFK-ORD
2h 52mnonstop
1:35 pm - 4:58 pmORD-JFK
2h 23mnonstop
$510Delta
Find Deal
Tue, Mar 25 - Thu, Mar 27
7:29 pm - 9:24 pmJFK-ORD
2h 55mnonstop
7:35 am - 10:55 amORD-JFK
2h 20mnonstop
$519Delta
Find Deal
Thu, Feb 27 - Sun, Mar 30
10:46 am - 4:58 pmSFO-ORD
4h 12mnonstop
7:00 pm - 10:10 pmORD-SFO
5h 10mnonstop
$897Hawaiian Airlines
Find Deal
Tue, Mar 11 - Thu, Mar 13
9:10 am - 9:59 pmSFO-ORD
10h 49m1 stop
6:58 pm - 9:57 pmORD-SFO
4h 59mnonstop
$920Alaska Airlines
Find Deal
Tue, May 6 - Fri, May 9
11:48 am - 6:20 pmSFO-ORD
4h 32mnonstop
6:58 pm - 9:57 pmORD-SFO
4h 59mnonstop
$1,003Hawaiian Airlines
Find Deal
Fri, Apr 25 - Sun, Apr 27
6:49 pm - 6:05 amSFO-ORD
9h 16m1 stop
6:58 pm - 9:57 pmORD-SFO
4h 59mnonstop
$1,035Alaska Airlines
Find Deal
Fri, Apr 25 - Sun, Apr 27

Good to Know - First Class Flights to Chicago

Low season

January

High season

August

Average price round-trip

$1,103

Good deal round-trip

$495

Good deal one-way

$445
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 10% 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 37m
    Flights from New York2h 26m
    Flights from Denver2h 41m
    Flights from Boston2h 42m
    Flights from Miami3h 21m
  • 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 8.1.

See more FAQs

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 Friday.
See more tips

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.
8.1
SouthwestOverall score based on 4482 reviews
7.6Entertainment
8.7Crew
7.1Food
8.2Boarding
8.1Comfort
Airline reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

10.0 ExcellentAnonymous, Jan 2025ATL - LGA
Read more Southwest reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

It was 2 hours 45 minutes late, for no apparently clear reason.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

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.

They left my luggage behind in Seattle. However, they delivered it to my home the next morning.

The whole process was very smooth. My only complaint was finding out the evening before our flight that I had 20 hours left to purchase in flight food. Was not made aware of thus option prior to that alert and was too busy with other preparations to participate.

All good except both the outbound and return flights were delayed about 1 1/2 hrs.

Not great. My flight was canceled due to a mechanical problem and I could not get rebooked for the same day. I needed to get to my destination yesterday, not today. I was able to book with another airline but it was a layover and ultimately a 1 hour flight took me 12 hours. Normally I like Alaska much more than Southwest, but Southwest came through with a not terrible price for same day.

Alaska Airlines fraudulently listed this as a direct flight to Pittsburgh. We landed in Cleveland, waited an hour, then flew to PIT. No one was told about this. When I called and spoke with Alaskan Airways customer care, they were extremely unhelpful and lied about the direct flight. I have my receipt showing a direct flight. I am in the process of working with my credit card because Alaskan Airlines misrepresented the sale/service. I will never do business with Alaskan Airlines again.

You guys are always have delays and then leaving us on the tarmac for 15-20 min. FIGURE IT OUT!

It was raining and cold and we had to walk outside to board the plane. And to have yo stand outside to wait in line to board. It seems they could find another way to send a few people at a time so passengers are not outside in the elements. Then to not have my luggage show up at my finally destination. Not happy with the whole experience.

The plane was late arriving. The Alaska people did a great job of turning it around quickly and getting us off. We took off about 35 minutes after it reached the gate.

I liked the flight attendant named Tyler. He was charismatic and genuine. I like the pilot in my second flight, he was considerate to everyone’s feelings. I liked the people I sat beside. I like the plane size. I like Alaska airlines

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

Kind staff. Snacks are small but that’s the new normal.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

I like in St George and prefer to fly out of CDC than SGU. Hopefully, they will continue the flights out of Cedar

Broken jer bridge. Poor communication about it. Lost 2 of 4 luggage pieces

Overall, it was okay. Seat was a little cramped. Would’ve liked more substantial snacks or opportunity to buy some.

Boarding was a nightmare. Almost everyone was on group 4 and there was no line people crowded the check in and made things more chaotic than they needed to be.

A330-200 is very comfortable - lavatory roomier then Narrow Body jets.

Hawaiian airlines canceled my flight the night before my a due to weather. This is fine, I know this happens. In the email alerting me to the cancellation they said they would reach out to reschedule. I got this email at dinner time the night before the trip. I didn’t hear back so I called and was on hold for hours, I tried their texting questions option and never heard back. I tried to chat with a representative online, the website says you can chat and have questions answered but there is no link to a chat option anywhere on the site. After hours trying to get someone to communicate with me about the details of the cancellation and my rescheduling options I have up, got the flight refunded and booked a much more expensive last minute flight. Nonexistent customer service, I’ll never fly Hawaiian again.

The flight crew did what they could to make things as comfortable as possible.

The flight crew made the trip pleasant considering they had to work in conditions similar to a sardine can.

Having enough fuel to get to our destination seems like it should be a given when you board a plane. Not in this case, delayed hours to refuel.

Friendly & on Time .Need to make sure the Hana Hou magazine is in front of each seat

The leg room, complementary WiFi and food and drinks. Friendly staff

It would have been better if the airlines would of have the gate ready to go instead of waiting 30 minutes for the other airplane to take off

Everything for a 9:30 hour flight was fine. Seats are not very large, but worked. You should get up 2 or 3 times during that duration flight for your legs sake. Food needed more Protein meats for me. I have to check on a diabetic meal in future. I don't do sugar, so very little too eat. Flight was cheap so I am willing to look over other amenities. Everything else was great

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

No music app working: no economy meal on five hour flight; hour on tarmac at the end waiting for a gate. Flight itself was smooth and easy.

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Overall was excellent. Will definitely us JetBlue in the future.

I rate it is good we had a 4-hour travel delay at one point but JetBlue gave out food vouchers and travel points credits for another flight so they try to make up for it

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.