$125 Find Cheap Flights from Chicago to Tulum - 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 Tulum departing on 10/10. 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
$316
Typical prices: $327-$727
Viva
Wed 11/18Mon 11/23
ORD - CUN • 1 stop
Cheapest non-stop
$428
Typical prices: $329-$760
Frontier
Thu 11/12Mon 11/16
ORD - CUN • Non-stop
Arrival airport
You can't fly directly to Tulum. It is served by Cancún (CUN), located 68.6 miles from Tulum.
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Flight Deals
Useful Info
Flight Deals

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

Wed, Nov 18 - Mon, Nov 23
Viva Logo
12:35 am - 11:55 pm
ORD
-
CUN
22h 20m
1 stop
Viva Logo
7:00 am - 10:55 pm
CUN
-
ORD
16h 55m
1 stop
$316Viva
Sun, Nov 1 - Tue, Nov 24
Viva Logo
12:35 am - 11:55 pm
ORD
-
CUN
22h 20m
1 stop
Viva Logo
10:35 pm - 10:55 pm
CUN
-
ORD
25h 20m
1 stop
$316Viva
Fri, Nov 6 - Fri, Nov 13
Volaris Logo
6:23 am - 9:01 pm
ORD
-
CUN
13h 38m
1 stop
Volaris Logo
1:00 pm - 11:39 pm
CUN
-
ORD
11h 39m
1 stop
$317Volaris
Tue, Sep 15 - Tue, Sep 22
Volaris Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
Volaris Logo
10:50 am - 11:47 pm
CUN
-
ORD
12h 57m
1 stop
$317Volaris
Fri, Sep 18 - Thu, Sep 24
Multiple Airlines Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
Multiple Airlines Logo
12:35 pm - 11:40 pm
CUN
-
ORD
11h 05m
1 stop
$323Multiple Airlines
Sun, Sep 20 - Thu, Sep 24
Multiple Airlines Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
Multiple Airlines Logo
12:35 pm - 11:40 pm
CUN
-
ORD
11h 05m
1 stop
$323Multiple Airlines
Sun, Sep 20 - Thu, Sep 24
American Airlines Logo
6:00 am - 2:56 pm
ORD
-
CUN
8h 56m
1 stop
American Airlines Logo
2:57 pm - 7:07 pm
CUN
-
ORD
4h 10mnonstop
$380American Airlines
Tue, Sep 15 - Fri, Sep 18
American Airlines Logo
10:11 am - 2:00 pm
ORD
-
CUN
3h 49mnonstop
American Airlines Logo
4:25 pm - 12:33 am
CUN
-
ORD
8h 08m
1 stop
$385American Airlines
Wed, Dec 30 - Tue, Jan 12
Delta Logo
8:55 am - 4:00 pm
ORD
-
CUN
6h 05m
1 stop
Delta Logo
1:40 pm - 8:37 pm
CUN
-
ORD
7h 57m
1 stop
$397Delta
Sat, Oct 17 - Wed, Oct 28
Delta Logo
1:54 am - 8:28 pm
ORD
-
CUN
18h 34m
1 stop
Delta Logo
6:06 am - 2:07 pm
CUN
-
ORD
8h 01m
1 stop
$442Delta
Useful Info

Good to know

Low season

September

Cheapest flight

$125
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 14% 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 35m.

  • 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 64 departures each week.

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

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

  • 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 5 days, the cheapest one-way ticket between Chicago and Tulum found on KAYAK was with Frontier for $87. Volaris offered a round-trip connection from $119 and Delta from $158.

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 61 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 November, December and January. The cheapest month to fly is January.

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 4227 reviews
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
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

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

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.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

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.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

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

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

All planes flying to Mexico City are very old. Seats don’t even have power outlets.

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.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

Overall a good red eye. Crew chatted very loudly the whole time making it difficult to sleep.

The fly was 2 hours delayed and the plane was old and dirty. A very umcorfotable flight, which I won't recomend to anyone

Confusion over extra fees. Held up on ramp during boarding. Thin seat cushion. Minimal leg room.

The check-in is either at a kiosk that didn’t allow me to check-in because my middle name was not on the reservation or at an agent that cost $15.

They don’t give anything for free you have to pay for everything which it’s expected but at least give out water and a snack as a courtesy for flying with them.

The app doesn’t work. I am having a lot of trouble checking in for flight tomorrow. Very disconcerting. Then they es t to charge extra for checking in at the airport;(

Overall good flight. The flight attendants were annoying and unfriendly. They would ask me to grab someone else’s trash can just waiting until the person woke up or after the flight is done. It’s not my job to pick up someone else’s trash. Especially when it’s not easily reachable.

To many extra fees, poor customer service and very uncomfortable flight. No leg room and seat wont recline.

Delayed 2 hours. Boarding line took more than 30 minutes. Flight was really hot and made sleeping on a red eye impossible. Not a pleasant experience.

The flight was 3 hrs delayed and no remorse from airline

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

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.

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

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