$123 Find Cheap Flights from Chicago to Gilbert - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Gilbert departing on 8/22. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$245
Typical prices: $215-$333
Southwest
Wed 9/23Sat 9/26
MDW - PHX • Non-stop
Cheapest one-way
$123
Typical prices: $158-$188
Southwest
Sat 8/22
MDW - PHX • Non-stop
Arrival airport
You can't fly directly to Gilbert. It is served by Phoenix (PHX), located 13.3 miles from Gilbert.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Gilbert (CHI-PHX)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Gilbert that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Gilbert

Wed, Sep 23 - Sat, Sep 26
Southwest Logo
8:20 pm - 9:55 pm
MDW
-
PHX
3h 35mnonstop
Southwest Logo
4:55 pm - 10:15 pm
PHX
-
MDW
3h 20mnonstop
$245Southwest
Wed, Aug 19 - Tue, Aug 25
American Airlines Logo
10:35 pm - 12:14 am
ORD
-
PHX
3h 39mnonstop
American Airlines Logo
11:45 pm - 5:24 am
PHX
-
ORD
3h 39mnonstop
$245American Airlines
Sat, Aug 22 - Mon, Aug 24
Frontier Logo
11:45 am - 6:31 pm
MDW
-
PHX
8h 46m
1 stop
Frontier Logo
12:19 pm - 10:47 pm
PHX
-
MDW
8h 28m
1 stop
$246Frontier
Thu, Aug 13 - Wed, Aug 19
American Airlines Logo
1:59 pm - 3:41 pm
ORD
-
PHX
3h 42mnonstop
American Airlines Logo
6:52 am - 12:44 pm
PHX
-
ORD
3h 52mnonstop
$246American Airlines
Thu, Oct 15 - Mon, Oct 19
Frontier Logo
4:00 pm - 5:59 pm
ORD
-
PHX
3h 59mnonstop
Frontier Logo
6:30 am - 5:42 am
PHX
-
ORD
21h 12m
1 stop
$247Frontier
Sat, Aug 22 - Sat, Aug 29
Frontier Logo
11:45 am - 6:31 pm
MDW
-
PHX
8h 46m
1 stop
Frontier Logo
9:10 am - 10:47 pm
PHX
-
MDW
11h 37m
1 stop
$248Frontier
Sat, Aug 22 - Thu, Aug 27
Frontier Logo
2:41 pm - 9:28 pm
ORD
-
PHX
8h 47m
1 stop
Frontier Logo
9:10 am - 12:49 am
PHX
-
ORD
13h 39m
1 stop
$248Frontier
Fri, Sep 11 - Sun, Sep 13
Frontier Logo
12:03 pm - 9:39 pm
MDW
-
PHX
11h 36m
1 stop
Frontier Logo
10:44 pm - 10:58 am
PHX
-
MDW
10h 14m
1 stop
$249Frontier
Fri, Sep 11 - Mon, Sep 14
United Airlines Logo
9:12 am - 11:08 am
ORD
-
PHX
3h 56mnonstop
United Airlines Logo
8:45 am - 2:28 pm
PHX
-
ORD
3h 43mnonstop
$250United Airlines
Thu, Aug 20 - Sat, Aug 22
United Airlines Logo
12:47 pm - 5:56 pm
ORD
-
PHX
7h 09m
1 stop
United Airlines Logo
2:19 pm - 7:58 pm
PHX
-
ORD
3h 39mnonstop
$251United Airlines
Useful Info

Good to know

Low season

August

Cheapest flight

$123
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from Chicago Midway Airport to Phoenix Sky Harbor Airport

When to book flights from Chicago to Gilbert

Are your dates flexible? Find out the best times to travel from Chicago to Gilbert based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Flights from Chicago to Gilbert: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew the route from Chicago to Gilbert 
JanieFlew with SWISS
ORD
-
PHX
Feb 2025
I think you should prebook food or bring your own food.
Verified travelerFlew with United Airlines
ORD
-
PHX
Apr 2024
Use the find my gate feature on the flights phone app if available as the airport is a bit confusing

FAQs for booking flights from Chicago to Gilbert

  • Which airports will I be using when flying from Chicago to Gilbert?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway, Chicago O'Hare Intl or Chicago Greater Rockford. Gilbert does not have its own airport so you’ll be flying into nearby Phoenix Sky Harbor Intl airport, which is 13.3 mi away.

  • How long does a flight from Chicago to Gilbert take?

    Direct flights cover the 1,447 miles separating Chicago and Gilbert in about 3h 32m.

  • How many flights are there between Chicago and Gilbert?

    81 direct flights run between Chicago and Gilbert on a daily basis. On average, there are about 569 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Gilbert?

    Consider leaving on a Saturday and avoid Tuesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Tuesdays.

  • How does KAYAK find such low prices on flights from Chicago to Gilbert?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Gilbert.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Gilbert?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Gilbert from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Gilbert?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Gilbert with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Gilbert?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Gilbert from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Gilbert?

    In the last 5 days, the cheapest one-way ticket between Chicago and Gilbert found on KAYAK was with Frontier for $35. Frontier offered a round-trip connection from $64 and Delta from $108.

Top tips for finding cheap flights from Chicago to Gilbert

  • There is no airport in Gilbert. Instead, you’ll be flying into Phoenix Sky Harbor Airport when flying between Chicago and Gilbert.
  • The cheapest flight from Chicago to Gilbert was found 60 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be May, June and July. The cheapest month to fly is January.

Reviews of the top 5 airlines serving Chicago to Gilbert

 
Need help choosing which airline to fly with from Chicago to Gilbert? 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.
8.0
SouthwestOverall score based on 4231 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

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.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight was delayed but they still boarded us early knowing we were delayed. Were not able to move about the plane the majority of the flight.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

I liked the snacks and the flight attendants were friendly.

Other than a way way too cold cabinets for the entire flight, all was great

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

The flight experience was very good! Especially the United Club!

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Boarding crew at the gate were hilarious and made boarding run.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Regarding the boarding: it needs more efforts to make it more convenient

Plane was delayed multiple times. I would like to request a refund. Was due to arrive Thursday evening ended up arriving Friday morning.

The seats were roomier than other airplanes I’ve been on.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

The flight was delayed. I upgraded to more room. I can't imagine how small the regular seats are I haven't upgraded for my return flight yet.

Horrible - for the first time in my life i was denied boarding an international flight because the name used on my ticket - Josh - was not exactly the same as my passport - Joshua. At no time during ticketing, online check-in, or at the airport flying from Boston to NY was i notified of a problem. It was only at boarding from NY to Costa Rica I was informed of the problem and by then it was too late. After missing the flight I was told by airport Jet Blue staff, including a supervisor, that it was my problem and they could not assist because i bought "the cheapest fare". i was hung up on twice by JetBlue customer service, including once by a supervisor. I blame Kayak and your awful partner ChatDeal for even allowing me to purchase an international ticket without verifying this - you effectively sold me a ticket i could not use. Shame on you and shame on ChatDeal for doing nothing to help me resolve the situation. What a scam.

Like the variety of entertainment options. One crew member was a little on the rough/rude side. Boarding was a mess, attendants didn't do a great job of helping with the luggage storage and it delayed us a couple of minutes.

Given us a free miles or free flight for waiting for 9 hours I didn’t get home till 5am in the morning and I was supposed to be home at 9:30 touch down.

I had back trouble prior to my flight and everyone was great about helping me.

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 !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Everything you need to know for your flight from Chicago to Gilbert

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