Consider Main Cabin Extra for early boarding and complimentary drinks on longer flights.
Basic Economy offers low fares but includes restrictions like late boarding and no seat assignment.
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Low season | February |
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High season | December |
Cheapest flight | $99 |
Find which airlines fly direct from Key West Airport to Chicago, which days they fly and book direct flights.
Direct departures
Key West to Chicago
Monday
Air New Zealand, American Airlines, Qatar Airways, +1 more
Air New Zealand, American Airlines, +2 more
1
Tuesday
Air New Zealand, American Airlines, Qatar Airways, +1 more
Air New Zealand, American Airlines, +2 more
1
Wednesday
Air New Zealand, American Airlines, Qatar Airways, +1 more
Air New Zealand, American Airlines, +2 more
1
Thursday
Air New Zealand, American Airlines, Qatar Airways, +1 more
Air New Zealand, American Airlines, +2 more
1
Friday
Air New Zealand, American Airlines, Qatar Airways, +1 more
Air New Zealand, American Airlines, +2 more
1
Saturday
Air New Zealand, American Airlines, Qatar Airways, +1 more
Air New Zealand, American Airlines, +2 more
1
Sunday
Air New Zealand, American Airlines, Qatar Airways, +1 more
Air New Zealand, American Airlines, +2 more
1
Direct returns
Chicago to Key West
Monday
Air New Zealand, American Airlines, United Airlines
Air New Zealand, American Airlines, +1 more
Tuesday
Air New Zealand, American Airlines, United Airlines
Air New Zealand, American Airlines, +1 more
Wednesday
Air New Zealand, American Airlines, United Airlines
Air New Zealand, American Airlines, +1 more
Thursday
Air New Zealand, American Airlines, United Airlines
Air New Zealand, American Airlines, +1 more
Friday
Air New Zealand, American Airlines, United Airlines
Air New Zealand, American Airlines, +1 more
Saturday
Air New Zealand, American Airlines, United Airlines
Air New Zealand, American Airlines, +1 more
Sunday
Air New Zealand, American Airlines, United Airlines
Air New Zealand, American Airlines, +1 more
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.
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.
Flight left early and arrived early. the whole trip was excellent.
Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.
Everything was great. Great service, excellent communication, and early arrival
I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.
Good and consistent Printer in lounge did not work for me :(
Great - This was the last flight before hurricane closures and did a quick turnaround to get the plane heading north. Much appreciated.
I liked the screens in the seat headrest with movies to watch. I didn’t like being forced to check my carryon bag and being told there wasn’t room for my bag - when there were 5 bins sitting empty on takeoff. I didn’t like the “I don’t give a fig” attitude of the flight attendants and the delta gate attendants when I asked why they decided to put me out. They gave me a 1800 number to call but I can’t get a live person on the phone. Customer service is non existent. My business must not be that important to them.
It was not in Delta's control, but when we landed, we ended up parking at the wrong gate, and so everyone was already ready to deplane and had their carryon bags, ready to leave. But we had to sit down and move to the proper gate. This process took over 30 minutes. Again, not Delta's fault - more so on the staff at JFK
It’s was good. There’s so much room for improvement though. Since the plane was small, there was no entertainment but for years now, the most jarring aspect of travel is the lack of tasty snacks.
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
The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks
The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.
Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago
The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.
They canceled our flight and left us stranded to figure it out
Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done
Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA
As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.
Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.
Per usual, flight status, staff courtesy and professionalism were excellent
The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.
Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?
Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.
Delayed due to no crew. On a major holiday travel day.
Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.
It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.
The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.
The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.
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