Based on the flight data, it is generally cheaper to fly from Chicago to Phoenix Sky Harbor Airport on Saturdays in September.
Cheapest Route: Opt for flights from Chicago Midway to Phoenix Sky Harbor for the cheapest route.
Booking Time: Book your flight at least 140 days in advance for the best prices.
Cheapest Airline: Frontier Airlines generally offers the cheapest flights for this route.
Flight Type: Direct flights are more expensive, consider flights with layovers to save money.
AI-powered; AI can make mistakes.
| Low season | August |
|---|---|
| High season | March |
| Cheapest flight | $92 |
Direct departures
Chicago to Phoenix Sky Harbor Intl
Monday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
1
Tuesday
American Airlines,Southwest,United Airlines
American Airlines,Southwest, +1 more
Wednesday
American Airlines,Southwest,United Airlines
American Airlines,Southwest, +1 more
Thursday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
1
Friday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
1
Saturday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
1
Sunday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
1
Direct returns
Phoenix Sky Harbor Intl to Chicago
Monday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
1
Tuesday
American Airlines,Southwest,United Airlines
American Airlines,Southwest, +1 more
Wednesday
American Airlines,Southwest,United Airlines
American Airlines,Southwest, +1 more
Thursday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
1
Friday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
1
Saturday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
1
Sunday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
1
Had a great flight. Delayed takeoff, but comfortable. Snacks were good.
Had a great flight. Delayed takeoff, but comfortable. Snacks were good.
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.
I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.
Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.
Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !
I liked it better when you were truer to your roots Am paying more for less fun
Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.
I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.
Boarding was easy. The seats are small and fairly uncomfortable
I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.
Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.
Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.
I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.
The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat
Delta is always a wonderful experience. A clean plane and the crew is really friendly.
Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.
This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.
I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.
Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.
I am still at the Airport! Delayed Delayed and Delyaed
No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.
Terrible, if possible won't be flying again anytime soon!
Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.
Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)
Awful. No counter attendants. No dinner offered due to delays.
This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.
We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.
Short flight, but no drink/snack service. The flights both going and coming were delayed.
Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd
I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.
The flight attendant was friendly and efficient. The temperature was kept nice and cool. The plane was nice, but filthy. There were visible spills on my tray table. The gate agent was somewhat rude with her announcements and in speaking with other customers.
Great experience. Good dinner and service. FA's were very nice and attentive.
Mostly good. The WiFi wasn’t working so that was not great.
I like that the flight attendant was very attentive and helpful. The meal menu could have more of an variety of food choices.
The flight was fine, once we got underway. It was more than hour delayed
Arrived 40 min early which was great - sat in runway for 35 min so no gain. Then waited for luggage 45 min. They need to staff accordingly knowing its one of the busiest week in Phx
My flight got rerouted due to crew rest. I was sent to Dallas customer service was not very polite. Was given a $40 room voucher for Motel 6 and $12 to eat with. It delayed me by a day. Where if I would have just stuck with my original flight Arizona was delayed to Cleveland and I could have made it home. They put me on a 9:00 flight out of Dallas to Cleveland without my knowledge or consent. When originally I was told it would be 8:45 a.m. on February 1st. I told them I could not take the 9:00 flight because I did not have anybody to pick me up from the airport at that time. I'm extremely disappointed in how I was treated. And I will not fly American Airlines again.
It would be nice to have some low carb options in the snacks.
The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.
Trip delayed for 2 hours because of rain. We boarded and have to get down the flight and reboard again.
It was an early flight and most people napped/slept and the crew let us which was nice.
The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times
More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!
My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience
There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!
Remind customers of the need to have passport or new ID for boarding.
Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!
The flight never took off and we spent 7 hours at the airport
Gate not determined until I got to the airport - hard to plan the trip to the airport.
Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.