$117 Find Cheap Flights from Riviera Maya to Chicago

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 9/4. 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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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

Fri, Jul 11 - Mon, Jul 14
Spirit Airlines Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
Spirit Airlines Logo
6:00 am - 9:50 amORD-CUN
3h 50mnonstop
$220Spirit Airlines
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Fri, Jul 11 - Mon, Jul 14
Spirit Airlines Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
Spirit Airlines Logo
6:00 am - 9:50 amORD-CUN
3h 50mnonstop
$228Spirit Airlines
Find Deal
Fri, Oct 10 - Tue, Oct 14
American Airlines Logo
12:59 pm - 5:00 pmCUN-ORD
4h 01mnonstop
American Airlines Logo
9:45 am - 1:25 pmORD-CUN
3h 40mnonstop
$230American Airlines
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Thu, Sep 11 - Sat, Sep 20
American Airlines Logo
2:50 pm - 6:50 pmCUN-ORD
4h 00mnonstop
American Airlines Logo
7:15 pm - 11:46 amORD-CUN
16h 31m1 stop
$256American Airlines
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Fri, Jul 11 - Fri, Jul 18
 Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
 Logo
12:25 pm - 8:05 pmORD-CUN
7h 40m1 stop
Sat, Jul 26 - Sun, Aug 10
 Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
 Logo
12:25 pm - 9:35 pmORD-CUN
9h 10m1 stop
Tue, Aug 19 - Sun, Aug 24
United Airlines Logo
5:22 pm - 7:53 amCUN-ORD
14h 31m1 stop
United Airlines Logo
9:29 am - 1:14 pmORD-CUN
3h 45mnonstop
$266United Airlines
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Fri, Oct 10 - Tue, Oct 14
United Airlines Logo
1:43 pm - 12:14 amCUN-ORD
10h 31m1 stop
United Airlines Logo
10:43 am - 2:28 pmORD-CUN
3h 45mnonstop
$287United Airlines
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Wed, Jul 2 - Wed, Jul 9
Frontier Logo
11:05 am - 3:04 pmCUN-ORD
3h 59mnonstop
Frontier Logo
7:35 am - 11:30 amORD-CUN
3h 55mnonstop
$423Frontier
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Sat, Jun 28 - Sun, Jun 29
Frontier Logo
11:05 am - 3:04 pmCUN-ORD
3h 59mnonstop
Frontier Logo
6:30 am - 1:50 pmORD-CUN
7h 20m1 stop
$424Frontier
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Good to know

Low seasonFebruary
High seasonSeptember
Cheapest flight$117
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 37% 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.

Top 4 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 8790 reviews
7.0Entertainment
6.6Food
7.7Boarding
7.3Comfort
8.1Crew
Airline reviews

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

6.0 GoodAnonymous, Jun 2025MLI - ORD
Read more United Airlines reviews

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Flight 5 hours late. There was zero communication from Spirit (everyone was standing at the gate waiting to board for an hour+) and we were only able to find out about delay via the website. Crew made no attempt to apologize for the delay or even explain what happened once we finally left. Missed connection as a result of the delay and Spirit was not even able to be located at the airport to help rebook or find a hotel. They 100% disappeared and I am still trying to get a refund on the missed flight. So far all they’ve offered is a $30 credit. I can’t think of anything they’ve done right so far and recommend everyone avoid this airline. I understand delays happen but they’ve made no attempt to rebook my family (traveling with 3 kids) or make this right.

All was ok until my last flight, when I was stopped while boarding and they insisted they take my carry on bag and check it and charged me $99 to do so. This was my 4th flight and the carryon did not change, so I was shocked when they made me check it and proceeded to demand $99 to check it. I was furious. This airline advertises as cheap flights but they will attempt to charge extra for bags, seats, oxygen, whatever else they can find and no extras, you don’t even get water.

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

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

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

Horrendous. I do not recommend Frontier. The passengers lack manners and decency, and the flight attendants lack professionalism. If I wasn’t in a bind to fly with 48 hours notice for a job interview, I would not have selected a flight with Frontier and I never plan to fly with them in the future.

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