$100 Find Cheap Flights from Chicago to Tulum

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 Tulum departing on 9/20. 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.
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1 adult, Economy

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Cheap Flights from Chicago to Tulum (CHI-CUN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Tulum 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 Tulum

Sun, Sep 14 - Thu, Sep 18
Spirit Airlines Logo
5:05 am - 12:59 pmORD-CUN
7h 54m1 stop
Spirit Airlines Logo
2:07 pm - 10:48 pmCUN-ORD
8h 41m1 stop
$238Spirit Airlines
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Mon, Sep 29 - Sat, Oct 4
Spirit Airlines Logo
5:17 pm - 8:11 amORD-CUN
14h 54m1 stop
Spirit Airlines Logo
2:07 pm - 10:48 pmCUN-ORD
8h 41m1 stop
$239Spirit Airlines
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Sat, Nov 8 - Wed, Nov 12
Spirit Airlines Logo
8:50 pm - 10:42 amORD-CUN
12h 52m1 stop
Spirit Airlines Logo
1:35 pm - 9:00 pmCUN-ORD
8h 25m1 stop
$240Spirit Airlines
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Sat, Oct 18 - Sat, Oct 25
Frontier Logo
8:05 am - 11:56 amORD-CUN
3h 51mnonstop
Frontier Logo
1:06 pm - 5:14 pmCUN-ORD
4h 08mnonstop
$253Frontier
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Sat, Oct 18 - Sat, Oct 25
Frontier Logo
8:05 am - 11:56 amORD-CUN
3h 51mnonstop
Frontier Logo
1:06 pm - 5:14 pmCUN-ORD
4h 08mnonstop
$254Frontier
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Tue, Oct 28 - Sat, Nov 1
Southwest Logo
9:40 am - 1:15 pmMDW-CUN
3h 35mnonstop
Southwest Logo
12:00 pm - 3:35 pmCUN-MDW
3h 35mnonstop
$271Southwest
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Sun, Nov 16 - Wed, Nov 19
Southwest Logo
10:40 am - 3:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
1:45 pm - 4:30 pmCUN-MDW
3h 45mnonstop
$276Southwest
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Fri, Feb 13 - Tue, Feb 17
Volaris Logo
11:58 pm - 3:01 pmORD-CUN
14h 03m1 stop
Volaris Logo
10:13 pm - 4:36 amCUN-ORD
7h 23m1 stop
$278Volaris
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Mon, Oct 27 - Fri, Oct 31
United Airlines Logo
8:43 am - 12:33 pmORD-CUN
3h 50mnonstop
United Airlines Logo
11:28 am - 9:17 pmCUN-ORD
9h 49m1 stop
$281United Airlines
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Mon, Oct 20 - Fri, Oct 24
United Airlines Logo
10:43 am - 2:28 pmORD-CUN
3h 45mnonstop
United Airlines Logo
3:38 pm - 7:36 pmCUN-ORD
3h 58mnonstop
$285United Airlines
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Good to know

Low seasonSeptember
Cheapest flight$100
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 21% increase in price.
Flight from Chicago O'Hare Airport to Cancun

When to book flights from Chicago to Tulum

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

FAQs for booking flights from Chicago to Tulum

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

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Tulum does not have its own airport so you’ll be flying into nearby Cancun airport, which is 68.6 mi away.

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

    Direct flights cover the 1,440 miles separating Chicago and Tulum in about 3h 29m.

  • How many flights are there between Chicago and Tulum?

    7 direct flights run between Chicago and Tulum on a daily basis. On average, there are about 49 departures each week.

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

    Consider leaving on a Sunday and avoid Mondays 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 Fridays.

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

    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 Tulum.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Tulum 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 Tulum?

    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 Tulum 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 Tulum?

    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 Tulum 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 Tulum?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Tulum found on KAYAK was with Spirit Airlines for $100. Spirit Airlines offered a round-trip connection from $238 and Frontier from $253.

Top tips for finding cheap flights from Chicago to Tulum

  • There is no airport in Tulum. Instead, you’ll be flying into Cancun Airport when flying between Chicago and Tulum.
  • The cheapest flight from Chicago to Tulum was found 66 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly is September.

Reviews of the top 5 airlines serving Chicago to Tulum

 
Need help choosing which airline to fly with from Chicago to Tulum? 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 4246 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

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

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

The staff was very very rude in Las Vegas when boarding the flight. When presenting the boarding ticket. Las Vegas flight, it was hot and stuffy, it smelled really bad.

Dear All, I have harassment and accident with the flight attendant . This is my phone to talk 8168073567, please, leave phone message . Regards Emily,

The incoming plane ✈️ was delayed 5 hours en route to Raleigh. My flight was delayed for 5 hours 😢. Finally boarded and then de boarded due to an AC problem. A very tough and long night.

Flight was on time but the amount of noise from several children and the kicking of my seat the entire flight was overwhelming.

I liked the check in procedure. The luggage charges and overweight cost can be better.

The flight was delayed be over 3 hours. I tried to get a refund for Vivian Kirby and my session kept being stopped. I was NEVER able to finish the prosses...after 2 hours of attempting.

Again, when I use Kayak I expect to pay the total amount and that´s it. Someone added an additional charge few days later after purchasing the tickets.

My experience with Spirit was good, but the experience with Kayak was not. Based on the Spirit agent Kayak added an additional charge after purchasing the tickets. When I buy the tickets I paid the total amount and I only pay once. This time they added an additional charge because based on Spirit they partially charge the tickets and I still needed to pay a second time. This is not good at all and Unprofessional

Spirit gets such a bad rap. I have never had a bad experience with them and the crew is always friendly and funny. This trip I had knee replacement surgery surgery 10 weeks ago. It is still a little rough to get get from point a to point b. And Spirit was on top of it. When there was a seat available the stewardess asked me if I wanted to move to an open seat so I could elevate my leg on the empty seat? 5 stars all around. They helped me on and helped me off the plane. I can’t say enough about the crew!!

We liked the woman who worked our gate and waited with us for our plane. We changed gates 3 times. Our flight was supposed to leave at 11:28am. We actually left after 5pm. It was not a good situation. This delay cost us a lot of money.

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

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

The worst. They don’t follow procedure for boarding per group. Flight got delayed for no understandably reasons, they changed our destination from PR to Miami, left us inside a plane for more than 8 hours, then cancelled flight in Miami leaving us stranded. Poorly managed re-accommodation for a new flight and overnight stay so I have to spend in a new ticket and my own hotel room to been able to get to my office next day. Lost 2 days of work and as a doctor, patients loosing their appointments. to other flights and besides

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