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Cheap flights from Riviera Maya to Chicago (CHI)

CUN — CHI
Jun 18 — Jun 251
Thu 6/18
Thu 6/25
1 adult, Economy
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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 May 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Kiwi.com)

One-way from

$133
(Super.com)

Popular in

September

Cheapest in

April

Average price

$277
Provider with most accurate pricing for Cancun-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Cancun-Chicago (CHI) flights.
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From Riviera Maya to Chicago (CHI)
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One-way flight from Riviera Maya to Chicago (CHI)
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Highest demand for flights based on searches. 18% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in May 2026
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Cheapflights Insights

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

How far ahead should I book a flight from Riviera Maya to Chicago?

The best time to book flights from Riviera Maya to Chicago is 78 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, June is the cheapest month in which you can book a flight from Riviera Maya to Chicago (average of $52). Flying from Riviera Maya to Chicago in September is currently the most expensive (average of $167). 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 May 19, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 63% on flights from Riviera Maya to Chicago by exploring options for tickets in the evening.

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 May 19, 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
7.9
Good
4,284 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

7.9

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
7.9
Good
4,284 reviews
Southwest
7.9
Good
4,284 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

7.9

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
9,733 reviews
Southwest
7.9
Good
4,284 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

7.9

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
11,645 reviews
Southwest
7.9
Good
4,284 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

7.9

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
6.2
Okay
8,612 reviews
Southwest
7.9
Good
4,284 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

7.9

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
2,945 reviews
Southwest
7.9
Good
4,284 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

7.9

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 6h 23m. Fly via Delta or United Airlines to get the fastest option. Airlines will cover a distance of 1483 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 $107. Spirit Airlines flights start at $114 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 Spirit Airlines (76%), Emirates (71%) or American Airlines (64%) 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 $133. On average you can expect to pay $360. The most popular route, (Cancun - Chicago O'Hare Intl), can usually be booked for $321.

  • 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, June is the cheapest month in which you can book a flight from Riviera Maya to Chicago (average of $52). Flying from Riviera Maya to Chicago in September is currently the most expensive (average of $167). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 May 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$142Average$184FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$147Average$231FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$209Average$315FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$271Average$352FlexibilityNo cancel feeOn-time71%

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