$87 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 7/21. 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

Mon, Aug 11 - Fri, Aug 15
 Logo
6:00 am - 9:50 amORD-CUN
3h 50mnonstop
 Logo
11:05 am - 3:06 pmCUN-ORD
4h 01mnonstop
Sat, Aug 23 - Sat, Aug 30
Volaris Logo
6:45 am - 10:36 amORD-CUN
3h 51mnonstop
Volaris Logo
11:51 am - 3:52 pmCUN-ORD
4h 01mnonstop
$208Volaris
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Mon, Jul 21 - Fri, Jul 25
Spirit Airlines Logo
6:00 am - 9:50 amORD-CUN
3h 50mnonstop
Spirit Airlines Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
$211Spirit Airlines
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Sat, Aug 16 - Sat, Aug 23
Spirit Airlines Logo
6:10 am - 9:39 amORD-CUN
3h 29mnonstop
Spirit Airlines Logo
10:34 am - 2:49 pmCUN-ORD
4h 15mnonstop
$217Spirit Airlines
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Sun, Jul 13 - Thu, Jul 17
Southwest Logo
5:25 pm - 9:00 pmMDW-CUN
3h 35mnonstop
Southwest Logo
8:15 am - 11:50 amCUN-MDW
3h 35mnonstop
$270Southwest
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Sun, Sep 21 - Sat, Sep 27
Southwest Logo
10:35 am - 2:10 pmMDW-CUN
3h 35mnonstop
Southwest Logo
2:25 pm - 6:05 pmCUN-MDW
3h 40mnonstop
$275Southwest
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Mon, Aug 11 - Wed, Aug 13
Frontier Logo
4:01 pm - 2:12 pmMDW-CUN
22h 11m1 stop
Frontier Logo
3:25 pm - 8:54 pmCUN-MDW
29h 29m1 stop
$318Frontier
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Sat, Sep 27 - Wed, Oct 1
Delta Logo
11:00 am - 8:15 pmMDW-CUN
9h 15m1 stop
Delta Logo
8:10 am - 9:36 pmCUN-MDW
13h 26m2 stops
$323Delta
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Sat, Oct 18 - Sat, Oct 25
Delta Logo
6:00 am - 11:19 amMDW-CUN
5h 19m1 stop
Delta Logo
8:15 am - 9:44 pmCUN-MDW
13h 29m1 stop
$324Delta
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Fri, Jul 25 - Wed, Jul 30
Frontier Logo
6:40 pm - 11:18 amMDW-CUN
16h 38m1 stop
Frontier Logo
3:25 pm - 8:54 pmCUN-MDW
29h 29m1 stop
$335Frontier
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Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$87
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 22% 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?

    9 direct flights run between Chicago and Tulum on a daily basis. On average, there are about 68 departures each week.

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

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

  • 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 $87. Volaris offered a round-trip connection from $208 and Spirit Airlines from $211.

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 75 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 4266 reviews
8.2Boarding
7.6Entertainment
8.0Comfort
7.0Food
8.6Crew
Airline reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

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

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

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

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

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.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

We paid for upgrade seats (3A & 3B) the seats on front and the seats behind us got complimentary water & soda, but we got charged, had to pay for everything. Does not make any sense ?

Unfortunately, spirits crew had us boarding and parking the plane often, would wait long periods of time before allowing the people attending the flight on the plane to know what was going on this caused for my plane to not only get diverted but then canceled at an airport 2 hours away and basically stranded with charter buses MAYBE being hired. I was left with no choice but to stay overnight and use a comp room in Altantic City to then arrive home the next day. This trip was the first time seeing my partner since he joined the Air Force and this stressful ride caused unwarranted tears on what was supposed to be an east flight home. I understand weather is unpredictable but to have passengers deboard to then reboard an hour later to taxi on the runway for another hour to then basically leave an entire fight stranded. I waited almost 30 minutes at the airport and not one employee could tell me about a charter bus so I had to leave and make accommodations to stay overnight and get a ride home.

I wanted to upgrade my seat because I’m 6’2 and never have enough leg room for my comfort. They upgraded my seat for free putting me in an emergency exit seat. I was very comfortable

I have never flown Spirit it was much better than anticipated!

Staff was very friendly. They attended to people nicely and reprimanded, in a professional way, to those who wouldn’t listen. AC wasn’t working on the flight waiting to depart in Burbank, so it was uncomfortable for a while since the flight was delayed but then better before take off.

This was the first time I use Spirit Airlines and was pleasantly surprised. It was a last-minute booking and I was happy to see there was availability on your airline for a price that was affordable. The staff was friendly. The only things I thought were missing, were the ability to recline the seats, although I don’t use that very often, and it would’ve been nice to have power access at the seats to plug in my devices.

Flight was on time and was not crowded. Flight attendants were very understanding of my wife’s back problems.

Good on that leg. When I arrived in Detroit I had to wait over an hour for luggage.

Not very good because of an almost 3 hour delay for an hour long flight.

The spirit flight was on time. The airplane itself was surprisingly very nice. We had great seats. Seems like there's more room. Only complaint is that I didn't get a full refund for my mistakenly buying the baggage twice.

We’ve all seen the YouTube vids of out of control passengers. But this was an instance of a highly aggressive, bully flight attendant. Yelling in the face of a vet with PTSD who was texting their family. And no , we had not yet been instructed to put our phones in airplane mode. My suggestion is that you should pay whatever difference there is in order to avoid Frontier airlines. Additionally, after 3hrs trying to get customer service frontier offered a $25 voucher. I declined. This experience was so traumatic. To be verbally assaulted and abused by a flight attendant that has the power to say “boo” and I miss my flight ( which was to a family member’s funeral ). Frontier is unsafe and I cannot impress enough how much I discourage anyone ( esp those with any kind of disability like PTSD ) flying on Frontier.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

Very bad! No good service delayed my second connection flight

The confirmation # CK8GNW and my name was not recognized/in Frontier system. I was able to check in on Frintier app so i went to the Frontier ticket agent, at time they told me that my name/ confirmation did not show up as a purchased ticket. I had to purchase a new ticket that cost $289.00 one way.

Flight was late. Missed connecting in Denver. My new flight is more than 24 hours later and I have no room, vouchers, or compensation, and might also be bumped from the one tomorrow.

Frontier is terrible. Paid for exit row, not given exit row, refused to refund fee.

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

We had to wait in line over an hour just to check our bags. It's a good thing we were so early to the airport. Only one clerk was working and the line was around the corner and down the hall. No good. I felt bad for her. Not sure how she kept her sanity with all the upset people. Then we get to our gate and there is no seating. Everyone was standing. Then I realize it is not a gate at all, we still have to be shuttled to our airplane. Ugh. Then we were late taking off and missed a window of opportunity before the airport runways were shut down for some reason. (not frontier's fault the runway shut down.) The seats on the airline are crammed and there is no cushion. Never had a tighter seating arrangement while flying. My 6' 4" husband was absolutely miserable the whole time with knees digging in to the seat in front of him. You think you are getting a good deal on a ticket, and then wham! I had to pay 75 dollars for our checked bags and 75 dollars for a carry on. No other airline does that!!! And also, there is a 40 pound weight limit on checked bags... Would have been cheaper flying with another airline, and I would have at least gotten a snack and drink. Was thankful for the tiny cup of water at least.

This was one of the first frontier airline flights this spring that wasn't delayed. It actually left on time. Some of the flight crew did not look happy, they didn't smile when the passengers were boarding or getting off the plane, and the passengers initiated greetings, not the staff. To me this was an odd experience to have with any flight/airline. I had a bad experience booking this flight. The price didn't solidify until late hours into the night. Ever time I purchased the ticket, I either received a denial email or an error because the price has changed, but it was never reflected on the flyfrontier or kayak websites until way after midnight on the date of travel. This caused me anxiety and irritation with the websites. Then I noticed a mishap with my name on my voucher as I went to check in, it was incorrect. When I proceeded to correct it, Frontier had no easy, let alone free, way to remedy it. I couldn't correct my name without a $75 charge, I couldn't cancel my voucher to repurchase it with the correct name without a $100 charge, because it was too close to departure. Then calling frontier was nearly impossible to remedy the situation with a human. It's already difficult to want to choose frontier because of all the upcharges, but you feel kinda trapped into doing so because it's the more affordable airline.

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

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