$204 Find Cheap Flights from Riviera Maya to Chicago - Compare and Save

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Cheap Flights from Riviera Maya to O'Hare Intl

 
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, Oct 22 - Fri, Oct 30
Arajet Logo
12:35 pm - 11:40 pmCUN  Cancun-ORD Chicago O'Hare Intl
11h 05m1 stop Punta Cana
Arajet Logo
6:45 am - 4:49 pmORD  Chicago O'Hare Intl-CUN Cancun
10h 04m1 stop Punta Cana
$280Arajet
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
12:35 pm - 11:40 pmCUN  Cancun-ORD Chicago O'Hare Intl
11h 05m1 stop Punta Cana
Multiple Airlines Logo
7:35 am - 9:03 pmORD  Chicago O'Hare Intl-CUN Cancun
13h 28m1 stop Mexico City Benito Juarez
$303Multiple Airlines
Thu, Oct 22 - Mon, Oct 26
Arajet Logo
12:35 pm - 11:40 pmCUN  Cancun-ORD Chicago O'Hare Intl
11h 05m1 stop Punta Cana
Arajet Logo
4:30 am - 4:57 pmORD  Chicago O'Hare Intl-CUN Cancun
12h 27m1 stop Punta Cana
$305Arajet
Thu, Oct 22 - Mon, Oct 26
Frontier Logo
10:49 am - 2:50 pmCUN  Cancun-ORD Chicago O'Hare Intl
4h 01mnonstop
Frontier Logo
6:10 am - 9:58 amORD  Chicago O'Hare Intl-CUN Cancun
3h 48mnonstop
$313Frontier
Thu, Oct 1 - Mon, Oct 5
Volaris Logo
9:50 pm - 5:52 amCUN  Cancun-ORD Chicago O'Hare Intl
8h 02m1 stop Mexico City Benito Juarez
Volaris Logo
7:35 am - 9:03 pmORD  Chicago O'Hare Intl-CUN Cancun
13h 28m1 stop Mexico City Benito Juarez
$327Volaris
Thu, Sep 17 - Mon, Sep 21
Volaris Logo
5:40 pm - 4:54 amCUN  Cancun-ORD Chicago O'Hare Intl
11h 14m1 stop Morelia
Volaris Logo
7:35 am - 9:03 pmORD  Chicago O'Hare Intl-CUN Cancun
13h 28m1 stop Mexico City Benito Juarez
$329Volaris
Thu, Oct 22 - Fri, Oct 30
Frontier Logo
10:49 am - 2:50 pmCUN  Cancun-ORD Chicago O'Hare Intl
4h 01mnonstop
Frontier Logo
6:10 am - 10:08 amORD  Chicago O'Hare Intl-CUN Cancun
3h 58mnonstop
$360Frontier
Fri, Oct 9 - Fri, Oct 16
Frontier Logo
10:49 am - 2:50 pmCUN  Cancun-ORD Chicago O'Hare Intl
4h 01mnonstop
Frontier Logo
6:10 am - 9:58 amORD  Chicago O'Hare Intl-CUN Cancun
3h 48mnonstop
$360Frontier
Thu, Oct 22 - Mon, Oct 26
United Airlines Logo
12:11 pm - 4:04 pmCUN  Cancun-ORD Chicago O'Hare Intl
3h 53mnonstop
United Airlines Logo
7:20 am - 11:23 amORD  Chicago O'Hare Intl-CUN Cancun
4h 03mnonstop
$407United Airlines
Fri, Oct 30 - Tue, Nov 3
United Airlines Logo
2:11 pm - 6:13 pmCUN  Cancun-ORD Chicago O'Hare Intl
4h 02mnonstop
United Airlines Logo
8:40 am - 1:43 pmORD  Chicago O'Hare Intl-CUN Cancun
4h 03mnonstop
$407United Airlines
Useful Info

Good to know

Low season

August

Cheapest flight

$204
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly and prices are also 18% lower on average.
Flight from Cancun to Chicago O'Hare Airport

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 3 airlines serving 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 10123 reviews
7.3Comfort
7.7Boarding
7.1Entertainment
8.1Crew
6.7Food
Airline reviews

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

6.0 GoodRaghupathy, Aug 2026
Read more United Airlines reviews

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

ok, butt flght was delyed for 2,5h from Frankfurt, and next Flight to Columbuse same

Flight was great. Almost miss my connecting flight due to late departure from Haneda. Had to run all through airport in Chicago to make the flight. Experience was great for 1st time flyers using ANA Airlines.

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

Seats are complete BS for 10 hrs. The guy at counter canceled our return flight from europe. Lufthansa on the way back made United look like a trailer park gathering. If given the opportunity, I will never fly united again. Lufthansa seats werent much better to be fair but the service was a 10 out of 10. Incant express how difficult umited made my trip.

It was a great experience to fly with ANA, the sit is very comfortable.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

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.

Hate it. They do not provide any food or drinks during the flight, unless you pay. They also charge a ton of money to bring a carry on bag. And their customer service is the worst. I will never fly with them again.

The money you save flying volaris is not worth it

We had boarding passes for the next flight but we could not catch the flight in the small airport just because volaris closed the boarding at the counters an hour before for which we had to sepnd almost 3+ hours to catch next flight. There are hardly anyone who can speak english, but thank God, we have found an young man who could not only speak English but helped us book for the next flight. The air crafts are noisy and scary sometimes to hear that squeeking noises during the take off and during the flight. They do not even offer a cup of coffee for free in flight. The prices are super high and the services are zero. That’s pretty much for this airlines in summary.

Unfortunately it was not a good flight got canceled had to be at the airport all night long to get a different flight to another airport my first flight with Volaris was very bad. Poor services

In Mexico charges too much for my luggage and I ask for help and nothing one lady she just disappeared 😡😡😡😡😡never going to fly there

Better communication about delayed flight. I am thankful for a small credit for late flight.

Terrible. And they charged over $400 just for luggage. And threatened that I would loose my flight if I didn’t pay. So I didn’t have another choice but to pay.

I got to where I needed to go quickly. There were no amenities. And the seats were painful.

The flight was delayed an hour and a half, and they would not update the board on when the flight was supposed to take off. Once the plane arrived, they started the boarding process before the plane was even ready for the passengers so we had to wait another 45 minutes on the tarmac while we waited for the plane to be ready for us. In my opinion, there is no point in starting the boarding process when you are not ready to board the plane. This just causes a crowded gate with everyone from zone one and zone two standing up going nowhere.

The WiFi tv wasn’t working. The flight was over sold and moved several times. The gate assignment appeared on the screens right as we were supposed to board. Because of the flight being over sold we were almost stuck in Cancun for a couple of a days. The flight attendants were unfriendly and would wake you up to pick up other people’s trash.

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
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