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$141+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
May 2 — May 91
Sat 5/2
Sat 5/9
1 adult, Economy
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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 April 2, 2026.

This Frontier deal was found by Cheapflights users on 4/1. 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 4/2310:40 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Mon 4/276:30 am
ORD
-
CUN
Nonstop4h 08m
Frontier
Deal found 4/1$146
This Frontier deal was found by Cheapflights users on 4/1. 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 4/1510:40 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Sat 4/186:30 am
ORD
-
CUN
Nonstop4h 08m
Frontier
Deal found 4/1$168
This Frontier deal was found by Cheapflights users on 4/1. 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
Fri 5/89:42 pm
ORD
-
CUN
1 stop14h 22m
Frontier
Deal found 4/1$169
This Frontier deal was found by Cheapflights users on 3/31. 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 5/141:14 pm
CUN
-
ORD
1 stop9h 47m
Frontier
Mon 5/186:00 am
ORD
-
CUN
Nonstop4h 03m
Frontier
Deal found 3/31$173
This Frontier deal was found by Cheapflights users on 4/1. 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 5/71:14 pm
CUN
-
ORD
1 stop9h 47m
Frontier
Mon 5/116:00 am
ORD
-
CUN
Nonstop4h 03m
Frontier
Deal found 4/1$174
This Frontier deal was found by Cheapflights users on 3/31. 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 4/910:42 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Mon 4/136:30 am
ORD
-
CUN
Nonstop4h 08m
Frontier
Deal found 3/31$176
This Frontier deal was found by Cheapflights users on 3/31. 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.
Tue 4/1410:40 am
CUN
-
ORD
Nonstop4h 09m
Frontier
Sun 4/195:59 am
ORD
-
CUN
1 stop8h 57m
Frontier
Deal found 3/31$177
This Frontier deal was found by Cheapflights users on 3/31. 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 4/1612:04 pm
CUN
-
ORD
1 stop12h 48m
Frontier
Tue 4/216:30 am
ORD
-
CUN
Nonstop4h 08m
Frontier
Deal found 3/31$183
This Frontier deal was found by Cheapflights users on 3/30. 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 4/1612:04 pm
CUN
-
MDW
1 stop10h 18m
Frontier
Tue 4/216:10 am
MDW
-
CUN
1 stop8h 46m
Frontier
Deal found 3/30$203
This Expedia deal was found by Cheapflights users on 3/31. 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.
Sat 5/22:09 pm
CUN
-
MDW
1 stop8h 05m
Frontier
Wed 5/66:00 am
MDW
-
CUN
1 stop8h 07m
Frontier
Deal found 3/31$206
This Frontier deal was found by Cheapflights users on 4/1. 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 4/3010:34 am
CUN
-
MDW
2 stops23h 54m
Frontier
Wed 5/66:00 am
MDW
-
CUN
1 stop8h 07m
Frontier
Deal found 4/1$220
This Frontier deal was found by Cheapflights users on 3/30. 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.
Tue 3/311:47 pm
CUN
-
MDW
1 stop7h 07m
Frontier
Sat 4/48:30 am
MDW
-
CUN
Nonstop3h 50m
Frontier
Deal found 3/30$237

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 April 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$146
(Frontier)

One-way from

$141
(Frontier)

Popular in

September

Cheapest in

January

Average price

$264
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. 15% potential increase in price ($52 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 April 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 April 2, 2026.
Use the filters below to find and compare flights from Riviera Maya to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CancúnChicago

CUN - ORD

CUNORD

Cancun

Tue 4/14

12:55 pm-5:00 pm

Nonstop4h 05m

Chicago O'Hare Intl

Sun 4/19

5:48 am-12:33 pm

1 stop6h 45m

$258

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 5/8

3:43 pm-12:58 am

1 stop9h 15m

Chicago O'Hare Intl

Mon 5/11

11:00 pm-10:06 am

1 stop11h 06m

$262

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 4/24

8:00 am-4:26 pm

1 stop8h 26m

Chicago Midway

Mon 4/27

6:00 am-2:01 pm

1 stop8h 01m

$281

CancúnChicago

CUN - ORD

CUNORD

Cancun

Wed 5/13

12:11 pm-4:16 pm

Nonstop4h 05m

Chicago O'Hare Intl

Sat 5/16

10:31 am-2:26 pm

Nonstop3h 55m

$282

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 5/13

8:00 am-9:09 pm

1 stop13h 09m

Chicago Midway

Sat 5/16

10:45 am-8:16 pm

1 stop9h 31m

$293

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 5/21

3:02 pm-11:59 pm

1 stop8h 57m

Chicago O'Hare Intl

Tue 5/26

7:00 am-8:16 pm

2 stops13h 16m

$294

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 7/4

3:39 pm-10:17 pm

1 stop6h 38m

Chicago Midway

Thu 7/9

11:05 am-8:15 pm

1 stop9h 10m

$313

CancúnChicago

CUN - ORD

CUNORD

Cancun

Sat 7/4

10:55 am-6:42 pm

1 stop7h 47m

Chicago O'Hare Intl

Thu 7/9

8:03 am-8:15 pm

1 stop12h 12m

$313

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 7/30

12:35 pm-8:31 pm

1 stop7h 56m

Chicago O'Hare Intl

Mon 8/3

6:30 am-2:36 pm

1 stop8h 06m

$313

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 6/5

12:25 pm-12:15 am

1 stop11h 50m

Chicago O'Hare Intl

Sat 6/6

2:00 am-11:20 am

1 stop9h 20m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 55 resultsSorted by cheapest first
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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 $80). Flying from Riviera Maya to Chicago in June is currently the most expensive (average of $243). 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 April 2, 2026.

Unlike at noon, 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 April 2, 2026.

The most flights from zzETW to CHI are scheduled on a Monday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 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 April 2, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican 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
4,337 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,337 reviews
Southwest
8.0
Very good
4,337 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,533 reviews
Southwest
8.0
Very good
4,337 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,549 reviews
Southwest
8.0
Very good
4,337 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.3
Okay
8,576 reviews
Southwest
8.0
Very good
4,337 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
3,004 reviews
Southwest
8.0
Very good
4,337 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 United Airlines, Delta, or Volaris 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 Frontier, which is currently one of the cheapest options available, starting at $112. Spirit Airlines flights start at $113 while deals on Southwest start at $144 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 Volaris (74%), Frontier (70%) or American Airlines (68%) 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 $134. On average you can expect to pay $377. The most popular route, (Cancun - Chicago O'Hare Intl), can usually be booked for $223.

  • 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 $80). Flying from Riviera Maya to Chicago in June is currently the most expensive (average of $243). 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

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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 April 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$142Average$184FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$147Average$277FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$209Average$325FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$271Average$310FlexibilityNo cancel feeOn-time71%

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