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 | $97 |
Direct departures
Chicago to Phoenix Sky Harbor Intl
Monday
American Airlines,Southwest,United Airlines
American Airlines,Southwest, +1 more
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,Southwest,United Airlines
American Airlines,Southwest, +1 more
Friday
American Airlines,Southwest,United Airlines
American Airlines,Southwest, +1 more
Saturday
American Airlines,Southwest,United Airlines
American Airlines,Southwest, +1 more
Sunday
American Airlines,Southwest,United Airlines
American Airlines,Southwest, +1 more
Direct returns
Phoenix Sky Harbor Intl to Chicago
Monday
American Airlines,Southwest,United Airlines
American Airlines,Southwest, +1 more
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,Southwest,United Airlines
American Airlines,Southwest, +1 more
Friday
American Airlines,Southwest,United Airlines
American Airlines,Southwest, +1 more
Saturday
American Airlines,Southwest,United Airlines
American Airlines,Southwest, +1 more
Sunday
American Airlines,Southwest,United Airlines
American Airlines,Southwest, +1 more
Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.
Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.
Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.
The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.
no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.
First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.
Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.
Comfortable. Easy. No problems. Just wish they had gf options for snacks.
The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!
This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den
We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!
Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.
The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.
In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.
Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous
The flight was very good and the staff was very friendly and helpful!
The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..
Very easy to use and convenient, you can perform any action within the same portal
In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.
WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.
Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.
A long delay. Don't travel late in the day.
Super friendly with lots of drink options an entertainment. Friendly crew.
The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.
Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.
Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.
Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.
The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.
Poor communication, flight was delayed for preventable reasons. I missed my connection.
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!
Like: flights are on time, good boarding process Can improve: planes are old, improve entertainment and make space more comfortable
Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.
The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.
My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.
The SFO Lounge crew were amazing. The bartender Faris was great. Thanks!
On time flight, good communication about boarding, lines didn't form unnecessarily for boarding before their group was announced (kept aisles clear), friendly flight attendants and service
Good flight, seated and had a water within 5 minutes. Crew was hospitable.
I didn't go from Reno to Phoenix I ended up going from Reno to Dallas to Tucson because my flight rebooked because my Amtrak was late I tried notifying you guys I also don't know what you ask me about my flight because you guys didn't book my flight
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.
Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.
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
Plane was hot and miserable and the crew was rude!
12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink
They didn’t offer a water, even after I asked
They switched our terminal 3 times and we were delayed for four plus hours!!!
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!!!