HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$148+ Cheap flights from Riviera Maya to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
Mar 17 — Mar 241
Tue 3/17
Tue 3/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Riviera Maya to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Riviera Maya to Chicago

Cheapest flights from Riviera Maya to Chicago
Explore the most affordable flight options available from Riviera Maya to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 15, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/611:40 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Mon 3/96:30 am
ORD
-
CUN
Nonstop4h 04m
Frontier
Deal found 2/11$195
This Frontier deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:27 pm
CUN
-
ORD
Nonstop4h 10m
Frontier
Mon 2/236:10 am
ORD
-
CUN
Nonstop4h 04m
Frontier
Deal found 2/11$196
This Frontier deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/136:27 pm
CUN
-
ORD
Nonstop4h 10m
Frontier
Wed 2/188:00 am
ORD
-
CUN
Nonstop4h 17m
Frontier
Deal found 2/11$201
This Frontier deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/187:19 pm
CUN
-
ORD
Nonstop4h 09m
Frontier
Mon 2/236:10 am
ORD
-
CUN
Nonstop4h 04m
Frontier
Deal found 2/11$203
This Frontier deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/187:19 pm
CUN
-
ORD
Nonstop4h 09m
Frontier
Sun 2/226:10 am
ORD
-
CUN
Nonstop4h 04m
Frontier
Deal found 2/11$208
This Frontier deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1610:40 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Tue 4/215:01 am
ORD
-
CUN
1 stop9h 55m
Frontier
Deal found 2/12$217
This Expedia deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1510:40 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Sat 4/185:01 am
ORD
-
CUN
1 stop7h 25m
Frontier
Deal found 2/11$218
This CheapOair deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/610:40 am
CUN
-
ORD
Nonstop4h 09m
Multiple Airlines
Sun 5/177:35 am
ORD
-
CUN
1 stop13h 28m
Multiple Airlines
Deal found 2/11$225
This Frontier deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:40 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Sun 5/106:30 am
ORD
-
CUN
Nonstop4h 03m
Frontier
Deal found 2/12$229
This United Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1612:55 pm
CUN
-
ORD
Nonstop4h 05m
United Airlines
Tue 4/215:48 am
ORD
-
CUN
1 stop13h 31m
United Airlines
Deal found 2/13$233
This United Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/712:55 pm
CUN
-
ORD
Nonstop4h 05m
United Airlines
Mon 5/1110:45 pm
ORD
-
CUN
1 stop11h 21m
United Airlines
Deal found 2/12$234
This Delta deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/168:00 am
CUN
-
MDW
1 stop8h 29m
Delta
Tue 4/216:00 am
MDW
-
CUN
1 stop8h 01m
Delta
Deal found 2/14$280

Find flight deals from Riviera Maya to Chicago

Keep the following information in mind while searching for Riviera Maya to Chicago flight deals. Data was last updated February 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$195
(Kiwi.com)

One-way from

$148
(Flightnetwork)

Popular in

September

Cheapest in

January

Average price

$227
Provider with most accurate pricing for Cancun-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Cancun-Chicago (CHI) flights.
Search Deals
From Riviera Maya to Chicago (CHI)
Search Deals
One-way flight from Riviera Maya to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Riviera Maya to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 15, 2026.
Use the filters below to find and compare flights from Riviera Maya to Chicago that are best for you.

Fly from

Riviera Maya

Fly to

Chicago

Route

Depart

Return

Price

CancúnChicago

CUN - ORD

CUNORD

Cancun

Wed 4/15

10:40 am-2:49 pm

Nonstop4h 09m

Chicago O'Hare Intl

Sat 4/18

5:01 am-12:26 pm

1 stop7h 25m

$218

CancúnChicago

CUN - ORD

CUNORD

Cancun

Wed 5/6

10:40 am-2:49 pm

Nonstop4h 09m

Chicago O'Hare Intl

Sun 5/17

7:35 am-9:03 pm

1 stop13h 28m

$225

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 4/30

12:55 pm-5:00 pm

Nonstop4h 05m

Chicago O'Hare Intl

Sun 5/3

10:31 am-2:26 pm

Nonstop3h 55m

$233

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 4/30

12:55 pm-5:00 pm

Nonstop4h 05m

Chicago O'Hare Intl

Sun 5/10

7:52 am-11:45 am

Nonstop3h 53m

$233

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 5/7

12:55 pm-5:00 pm

Nonstop4h 05m

Chicago O'Hare Intl

Mon 5/11

10:45 pm-12:02 pm

1 stop13h 17m

$233

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 4/16

12:55 pm-5:00 pm

Nonstop4h 05m

Chicago O'Hare Intl

Tue 4/21

5:48 am-7:19 pm

1 stop13h 31m

$233

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 4/16

8:00 am-4:29 pm

1 stop8h 29m

Chicago Midway

Tue 4/21

6:00 am-2:01 pm

1 stop8h 01m

$280

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 4/23

8:00 am-4:26 pm

1 stop8h 26m

Chicago Midway

Mon 4/27

12:52 pm-8:15 pm

1 stop7h 23m

$280

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 4/1

11:15 am-10:31 pm

1 stop11h 16m

Chicago Midway

Wed 4/8

10:45 am-8:14 pm

1 stop9h 29m

$281

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/26

4:45 pm-10:31 pm

1 stop6h 46m

Chicago Midway

Sat 2/28

6:00 am-9:11 pm

1 stop14h 11m

$281

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 49 results
1
2
3
...
5

Best time to book a flight from Riviera Maya to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Riviera Maya with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Riviera Maya to Chicago

What is the cheapest month to book a flight from Riviera Maya to Chicago?

Currently, August is the cheapest month in which you can book a flight from Riviera Maya to Chicago (average of $79). Flying from Riviera Maya to Chicago in June is currently the most expensive (average of $245). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ETW to CHI?

Find hourly flight availability from Riviera Maya to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 15, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 64% on flights from Riviera Maya to Chicago by exploring options for tickets in the evening.

Weekly flight availability from Riviera Maya to Chicago

Explore weekly flight availability from Riviera Maya to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 15, 2026.

The most flights from zzETW to CHI are scheduled on a Saturday (16 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (10 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated February 15, 2026.
See what other customers who have flown with Southwest, United Airlines, and Spirit Airlines from Riviera Maya to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,286 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,294 reviews
Southwest
8.0
Very good
4,286 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,453 reviews
Southwest
8.0
Very good
4,286 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,051 reviews
Southwest
8.0
Very good
4,286 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Riviera Maya to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Riviera Maya to Chicago?

    There are many flights that can get you from Riviera Maya to Chicago in 4h 05m. Fly via Frontier, United Airlines, or Delta to get the fastest option. Airlines will cover a distance of 1447 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Riviera Maya to Chicago one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $112. Frontier flights start at $112 while deals on United Airlines start at $125 one-way.

  • What are the most popular routes from Riviera Maya to Chicago?

    When deciding which route to take from Riviera Maya to Chicago consider Cancun - Chicago O'Hare Intl, Cancun - Chicago Midway or Cozumel - Chicago O'Hare Intl as they are the most popular.

  • What are the most reliable airlines from Riviera Maya to Chicago?

    Consider Qatar Airways (70%), United Airlines (66%) or Volaris (65%) when booking your flight. These represent the most reliable airlines when flying from Riviera Maya to Chicago.

  • What are the cheapest flights from Riviera Maya to Chicago?

    The cheapest flight price from Riviera Maya to Chicago is $132. On average you can expect to pay $330. The most popular route, (Cancun - Chicago O'Hare Intl), can usually be booked for $233.

  • Can I find deals for flights from Riviera Maya to Chicago that include hotel bookings?

    Yes. In addition to deals on Riviera Maya to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Riviera Maya to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Riviera Maya to Chicago.

  • Can I find deals for business class flights from Riviera Maya to Chicago?

    Yes. Cheapflights offers flight deals from Riviera Maya to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Riviera Maya to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Riviera Maya to Chicago (average of $79). Flying from Riviera Maya to Chicago in June is currently the most expensive (average of $245). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Riviera Maya to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Cancún to O'Hare Intl flights
Cancún to Midway flights
Cozumel to O'Hare Intl flights
Cancún to St. Louis flights
Cozumel to St. Louis flights

Top 4 airlines flying from Riviera Maya to Chicago

Discover the top 4 airlines that operate flights from Riviera Maya to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$142Average$198FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$147Average$234FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$209Average$325FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$271Average$310FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.