$195 Find Cheap Flights from Riviera Maya to Chicago - 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 to O'Hare Intl departing on 9/8. 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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Cheap Flights from Riviera Maya to O'Hare Intl

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Riviera Maya to O'Hare Intl 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 Riviera Maya to O'Hare Intl

Thu, Sep 24 - Mon, Sep 28
Arajet Logo
12:35 pm - 11:40 pm
CUN
-
ORD
11h 05m
1 stop
Arajet Logo
5:30 am - 5:12 pm
ORD
-
CUN
11h 42m
1 stop
$231Arajet
Thu, Sep 24 - Mon, Sep 28
Arajet Logo
12:35 pm - 11:40 pm
CUN
-
ORD
11h 05m
1 stop
Arajet Logo
5:30 am - 5:12 pm
ORD
-
CUN
11h 42m
1 stop
$249Arajet
Thu, Sep 24 - Mon, Sep 28
Arajet Logo
12:35 pm - 11:40 pm
CUN
-
ORD
11h 05m
1 stop
Arajet Logo
5:30 am - 5:12 pm
ORD
-
CUN
11h 42m
1 stop
$250Arajet
Thu, Oct 22 - Mon, Oct 26
Volaris Logo
10:50 am - 11:47 pm
CUN
-
ORD
12h 57m
1 stop
Volaris Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
$269Volaris
Thu, Sep 24 - Mon, Sep 28
Arajet Logo
12:35 pm - 11:40 pm
CUN
-
ORD
11h 05m
1 stop
Arajet Logo
5:30 am - 5:12 pm
ORD
-
CUN
11h 42m
1 stop
$271Arajet
Wed, Oct 21 - Mon, Oct 26
Volaris Logo
3:20 pm - 5:52 am
CUN
-
ORD
14h 32m
1 stop
Volaris Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
$272Volaris
Thu, Sep 3 - Sat, Sep 5
Multiple Airlines Logo
12:35 pm - 11:40 pm
CUN
-
ORD
11h 05m
1 stop
Multiple Airlines Logo
1:40 am - 10:03 am
ORD
-
CUN
8h 23m
1 stop
$280Multiple Airlines
Tue, Aug 25 - Fri, Aug 28
Volaris Logo
4:32 pm - 12:55 am
CUN
-
ORD
8h 23m
1 stop
Volaris Logo
6:21 am - 3:28 pm
ORD
-
CUN
9h 07m
1 stop
$282Volaris
Thu, Oct 1 - Tue, Oct 6
Multiple Airlines Logo
12:35 pm - 11:40 pm
CUN
-
ORD
11h 05m
1 stop
Multiple Airlines Logo
1:40 am - 10:03 am
ORD
-
CUN
8h 23m
1 stop
$284Multiple Airlines
Sun, Aug 16 - Mon, Aug 24
Viva Logo
8:30 pm - 11:55 pm
CZM
-
ORD
27h 25m
1 stop
Viva Logo
4:20 pm - 7:45 pm
ORD
-
CZM
27h 25m
1 stop
$491Viva
Useful Info

Good to know

Low seasonMay
Cheapest flight$195
Best time to beat the crowds but there is an average 39% increase in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Cozumel to Chicago

FAQs for booking Riviera Maya to Chicago flights

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

    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 Riviera Maya to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Riviera Maya 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 Riviera Maya to Chicago?

    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 Chicago with an airline and back to Riviera Maya with another airline.

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

    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 Chicago from Riviera Maya up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Riviera Maya to O'Hare Intl

 
Need help choosing which airline to fly with from Riviera Maya to O'Hare Intl? 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.
7.4
United AirlinesOverall score based on 9945 reviews
7.1Entertainment
7.3Comfort
8.1Crew
7.7Boarding
6.7Food
Airline reviews

Horrible experience. They delayed our flight 7 hours!! We had to seat at the airport with kids on 4th July all day!

2.0 MediocreBarbara, Jul 2026
PNS - ORD
Read more United Airlines reviews

Horrible experience. They delayed our flight 7 hours!! We had to seat at the airport with kids on 4th July all day!

The flight was delayed an hour and a half while you tried to fix the plane so I missed my connecting flight in Chicago. In Chicago, it took an hour to get the luggage. Then the conveyor belt was broken where I have to transfer my flight from an international flight to the continuing flight so I had to carry a large suitcase through the airport. The elevators were broken in the airport. I paid people to carry the luggage for me up the escalators in two different areas. The person who helped me get the new flight was outstanding. The temperature in the airport in Chicago was horrible. We were all sweating. It was the day from hell. That was after two hours in a security line in Athens. I have TSA pre-checked and global entry and I still waited. Two hours in a security line. Something has got to be done to stream line this service. After I’ve been through all of that in Athens, why do I have to go through it again in Chicago. It was the worst travel experience I have had in a long time. Your bathrooms have gotten so small that you can hardly get your butt on the toilet. You’ve taken the airspace out of the inside of the top of the toilet. It really makes for a miserable experience. Also on a 4 1/2 hour flight from Chicago to Los Angeles. The only thing we’re given is a bag of pretzels. REALLY!!

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Excellent all round, first time flying United. App is very helpful.

Unfortunately this is not a happy ending comment. Positive: flown United before no issue Negative: it only takes one bad experience to not plan future travel with United Cancún departure was delayed by 1h20 minutes, connection in Chicago was 1h30 minutes. Flight departure time 6:08 Miraculously 7 of us ran 4 kilometres through Chicago to arrive at 6:00 to be told very rudely by the 2 unprofessional United attendants you missed your flight and that we should of arrived early. Did I mention that reason I was flying? I received a call that my brother was dying and to get home. They provided no assistance would not answer any of our questions, ignorantly walked away. Deplorable

If United expects people to use their own devices for entertainment they should put charging outlets in each seating area. I arrived with 14%battery power. That is not good when you arrive anywhere and need to communicate for transportation.

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

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

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

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

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

Flying Frontier was a nightmare. From the booking through Kayak, checking in, departing and arriving, I will never recommend Kayak or Frontier.

Traveling to a place near O'Hare Intl?

Book flights to O'Hare Intl if you plan to visit one of these locations
Gurnee
Merrillville
South Haven
Oak Brook
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Tinley Park
Hammond
Elk Grove Village
Des Plaines
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Alsip
Lisle
Elmhurst
Valparaiso

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