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Flight Deals from Chicago Midway Airport to Cancun from $145

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Stops

  • Up to 1 stop
    $320
  • Up to 2 stops
    $464

Airlines

  • Aeromexico
    $320
  • Delta Air Lines
    $320
  • Frontier Airlines
    $341
  • Southwest Airlines
    $555
  • Virgin Atlantic
    $1129

Cabin Class

  • Economy
    $320

Departure Airports

  • Chicago Midway Airport
    $320

Arrival Airports

  • Cancún International Airport
    $320

Layover Airports

  • Baltimore/Washington International Thurgood Marshall Airport
    $555
  • Denver International Airport
    $436
  • Detroit Metropolitan Airport
    $598
  • Hartsfield Jackson Atlanta International Airport
    $320
  • Licenciado Benito Juarez International Airport
    $464
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $882
  • Orlando International Airport
    $444
  • Pittsburgh International Airport
    $555
  • San Antonio International Airport
    $612
  • St Louis Lambert International Airport
    $603
  • William P Hobby Airport
    $555

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Aeromexico Logo
Aeromexico

05/17/25

MDW
9h 55m
ATL

05/17/25

CUN
Aeromexico Logo
Aeromexico

05/24/25

CUN
8h 38m
ATL

05/24/25

MDW
$320
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/08/25

MDW
7h 32m
ATL

05/08/25

CUN
Delta Air Lines Logo
Delta Air Lines

05/22/25

CUN
7h 20m
ATL

05/22/25

MDW
$320
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

05/08/25

MDW
7h 32m
ATL

05/08/25

CUN
Aeromexico Logo
Aeromexico

05/13/25

CUN
10h 48m
ATL

05/13/25

MDW
$320
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/06/25

MDW
7h 57m
ATL

05/06/25

CUN
Delta Air Lines Logo
Delta Air Lines

05/20/25

CUN
7h 20m
ATL

05/20/25

MDW
$320
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/17/25

MDW
26h 40m
ATL

05/18/25

CUN
Frontier Airlines Logo
Frontier Airlines

05/20/25

CUN
3h 57m
Direct

05/20/25

MDW
$341
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/07/25

MDW
23h 16m
ATL

05/08/25

CUN
Frontier Airlines Logo
Frontier Airlines

05/14/25

CUN
3h 57m
Direct

05/14/25

MDW
$341
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

05/16/25

MDW
7h 32m
ATL

05/16/25

CUN
Aeromexico Logo
Aeromexico

05/21/25

CUN
7h 50m
ATL

05/21/25

MDW
$350
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/16/25

MDW
23h 43m
ATL

05/17/25

CUN
Frontier Airlines Logo
Frontier Airlines

05/17/25

CUN
3h 57m
Direct

05/17/25

MDW
$351
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/09/25

MDW
23h 43m
ATL

05/10/25

CUN
Frontier Airlines Logo
Frontier Airlines

05/13/25

CUN
3h 57m
Direct

05/13/25

MDW
$351
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

05/18/25

MDW
9h 45m
ATL

05/18/25

CUN
Aeromexico Logo
Aeromexico

05/21/25

CUN
7h 50m
ATL

05/21/25

MDW
$374
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/14/25

MDW
23h 16m
ATL

05/15/25

CUN
Frontier Airlines Logo
Frontier Airlines

05/17/25

CUN
3h 57m
Direct

05/17/25

MDW
$382
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/10/25

MDW
26h 40m
ATL

05/11/25

CUN
Frontier Airlines Logo
Frontier Airlines

05/15/25

CUN
8h 56m
ATL

05/15/25

MDW
$434
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/08/25

MDW
18h 48m
DEN

05/09/25

CUN
Frontier Airlines Logo
Frontier Airlines

05/22/25

CUN
8h 1m
ATL

05/22/25

MDW
$436
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

05/15/25

MDW
9h 55m
ATL

05/15/25

CUN
Aeromexico Logo
Aeromexico

05/20/25

CUN
10h 48m
ATL

05/20/25

MDW
$439
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/07/25

MDW
23h 16m
ATL

05/08/25

CUN
Frontier Airlines Logo
Frontier Airlines

05/14/25

CUN
27h 12m
DEN

05/15/25

MDW
$443
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/17/25

MDW
26h 40m
ATL

05/18/25

CUN
Frontier Airlines Logo
Frontier Airlines

05/31/25

CUN
10h 57m
MCO

05/31/25

MDW
$444
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

05/04/25

MDW
12h 7m
ATL
MEX

05/05/25

CUN
Aeromexico Logo
Aeromexico

05/14/25

CUN
12h 36m
MEX
ATL

05/14/25

MDW
$464
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/03/25

MDW
25h 28m
ATL

05/04/25

CUN
Frontier Airlines Logo
Frontier Airlines

05/07/25

CUN
27h 12m
DEN

05/08/25

MDW
$515
Free cancellation within 83 hours of booking
Southwest Airlines Logo
Southwest Airlines

05/22/25

MDW
25h 10m
BWI

05/23/25

CUN
Southwest Airlines Logo
Southwest Airlines

05/27/25

CUN
18h 20m
HOU
PIT

05/28/25

MDW
$555
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/22/25

MDW
46h 15m
ATL
MCO

05/24/25

CUN
Frontier Airlines Logo
Frontier Airlines

05/27/25

CUN
7h 54m
ATL

05/27/25

MDW
$573
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

05/24/25

MDW
7h 32m
ATL

05/24/25

CUN
Aeromexico Logo
Aeromexico

05/26/25

CUN
7h 51m
DTW

05/26/25

MDW
$598
Free cancellation within 83 hours of booking
Southwest Airlines Logo
Southwest Airlines

05/22/25

MDW
25h 10m
BWI

05/23/25

CUN
Southwest Airlines Logo
Southwest Airlines

05/27/25

CUN
6h 45m
STL

05/27/25

MDW
$603
Free cancellation within 83 hours of booking
Southwest Airlines Logo
Southwest Airlines

05/22/25

MDW
7h 25m
SAT
HOU

05/22/25

CUN
Southwest Airlines Logo
Southwest Airlines

05/27/25

CUN
18h 20m
HOU
PIT

05/28/25

MDW
$612
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

04/30/25

MDW
6h 46m
ATL

04/30/25

CUN
Delta Air Lines Logo
Delta Air Lines

05/14/25

CUN
10h 28m
ATL

05/14/25

MDW
$651
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

05/01/25

MDW
14h 20m
ATL
MEX

05/01/25

CUN
Aeromexico Logo
Aeromexico

05/05/25

CUN
9h 47m
ATL

05/05/25

MDW
$722
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

05/22/25

MDW
14h 24m
ATL
MEX

05/22/25

CUN
Aeromexico Logo
Aeromexico

05/27/25

CUN
7h 20m
ATL

05/27/25

MDW
$757
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

05/22/25

MDW
14h 5m
ATL
MEX

05/23/25

CUN
Aeromexico Logo
Aeromexico

05/27/25

CUN
12h 10m
MEX
ATL

05/27/25

MDW
$836
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

05/24/25

MDW
16h 40m
ATL
MEX

05/24/25

CUN
Aeromexico Logo
Aeromexico

05/28/25

CUN
15h 20m
MEX
ATL

05/28/25

MDW
$854
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/22/25

MDW
32h 13m
MSP
MEX

05/23/25

CUN
Delta Air Lines Logo
Delta Air Lines

05/27/25

CUN
13h 43m
MEX
ATL

05/27/25

MDW
$882
Free cancellation within 83 hours of booking
Virgin Atlantic Logo
Virgin Atlantic

05/22/25

MDW
14h 20m
ATL

05/22/25

CUN
Virgin Atlantic Logo
Virgin Atlantic

05/27/25

CUN
13h 43m
MEX
ATL

05/27/25

MDW
$1129
Free cancellation within 83 hours of booking

Top Deals on flights from Chicago Midway Airport to Cancun

Chicago, US (CHI) - Cancun, MX (CUN)

Aeromexico Logo
Aeromexico

Jul 12

MDW
11h 56m
ATL
MEX

Jul 13

CUN

as low as

$145

Chicago, US (CHI) - Cancun, MX (CUN)

Aeromexico Logo
Aeromexico

Jul 11

MDW
7h 42m
ATL

Jul 11

CUN

as low as

$145

Chicago, US (CHI) - Cancun, MX (CUN)

Aeromexico Logo
Aeromexico

Jul 2

MDW
9h 54m
ATL

Jul 2

CUN

as low as

$145

Chicago, US (CHI) - Cancun, MX (CUN)

Aeromexico Logo
Aeromexico

Aug 27

MDW
14h 28m
ATL
MEX

Aug 27

CUN

as low as

$179

Chicago, US (CHI) - Cancun, MX (CUN)

Frontier Airlines Logo
Frontier Airlines

May 23

MDW
10h 53m
MCO

May 24

CUN

as low as

$198

Chicago, US (CHI) - Cancun, MX (CUN)

Frontier Airlines Logo
Frontier Airlines

May 8

MDW
18h 48m
DEN

May 9

CUN

as low as

$198

Chicago, US (CHI) - Cancun, MX (CUN)

Frontier Airlines Logo
Frontier Airlines

Jun 9

MDW
14h 35m
PHL

Jun 10

CUN

as low as

$198

Chicago, US (CHI) - Cancun, MX (CUN)

Frontier Airlines Logo
Frontier Airlines

May 19

MDW
18h 7m
DEN

May 20

CUN

as low as

$198

Chicago, US (CHI) - Cancun, MX (CUN)

Frontier Airlines Logo
Frontier Airlines

May 29

MDW
6h 35m
ATL

May 29

CUN

as low as

$198

Chicago, US (CHI) - Cancun, MX (CUN)

Frontier Airlines Logo
Frontier Airlines

Jun 2

MDW
14h 35m
PHL

Jun 3

CUN

as low as

$198

Chicago, US (CHI) - Cancun, MX (CUN)

Southwest Airlines Logo
Southwest Airlines

Jul 26

MDW
3h 35m
Direct

Jul 26

CUN

as low as

$203

Chicago, US (CHI) - Cancun, MX (CUN)

Southwest Airlines Logo
Southwest Airlines

Jul 26

MDW
15h 50m
DEN

Jul 26

CUN

as low as

$208

Frequently Asked Questions

What is the typical flight duration from Chicago Midway Airport to Cancun?
The flight from Chicago Midway Airport to Cancun generally takes between 4 to 5 hours when flying direct, though it could be longer—up to 7 or 8 hours—if connecting flights are involved. This duration can vary with weather conditions and air traffic. It’s important to allot extra time for airport procedures and potential delays at both locations. Always check updated flight information when planning your trip to ensure a smooth journey between the two cities.
Are there any direct flights from Chicago Midway Airport to Cancun?
Yes, there are direct flights offered on this route from Chicago Midway Airport to Cancun, although availability may depend on the season and airline schedules. Direct services typically enable a faster travel time compared to connecting flights. However, flight frequency can fluctuate, so booking in advance and checking updated schedules is advised. When planning, you may also compare direct flights versus those with connections to balance cost and convenience based on your travel preferences.
What are the best transportation options from Cancun airport to downtown or popular tourist attractions?
From Cancun’s airport, travelers have multiple options to access downtown and major attractions. Express shuttles and private transfers are popular choices, with prices ranging from $20 to $50, depending on service level. ADO buses are an economical option, costing around $5 to $10 while offering frequent schedules and reliable service. Taxis and ride-sharing options are also available, though fares can vary. Always negotiate a fare or confirm rates before departure to ensure a hassle‐free transfer experience.
What are the must-see attractions in Cancun for travelers arriving from Chicago Midway Airport?
In Cancun, travelers can enjoy a blend of natural beauty and cultural experiences. Top attractions include the stunning beaches along the Hotel Zone, the Mayan ruins at El Rey, and the vibrant night scene at local hotspots. Nature enthusiasts should also consider a visit to the nearby Isla Mujeres and eco-parks like Xcaret. Each site offers unique insights into the area’s history and ecosystem. It’s advisable to set aside multiple days to experience both landmark sites and lesser-known local gems.
Which local dishes should travelers from Chicago Midway Airport try when visiting Cancun?
Travelers should definitely sample the local Mexican cuisine while in Cancun. Dishes such as cochinita pibil, a slow-roasted marinated pork, along with fresh ceviche and tacos de pescado are must-tries. Enjoying traditional fare like chiles en nogada and tamales in local eateries provides an authentic taste of the region. Dining at local markets or traditional restaurants can offer meals priced between $10 and $30 per dish. Each dish represents a delicious blend of indigenous flavors and culinary traditions.
What are the best family-friendly activities in Cancun for travelers from Chicago Midway Airport?
Cancun offers a variety of family-friendly activities that cater to all ages. Beach outings on the soft sands of the Hotel Zone, visiting interactive museums, or exploring eco-parks like Xel-Há provide engaging experiences. Water parks and snorkeling tours are also popular, with prices generally ranging from $20 to $60 per person depending on the activity. Families can organize day trips to nearby attractions such as the Mayan ruins or even boat tours to Isla Mujeres, ensuring that both younger and older travelers enjoy their adventure.
What are the most affordable dining options in Cancun for travelers from Chicago Midway Airport?
For cost-effective dining, explore local food stalls, traditional taquerias, and smaller eateries that offer authentic Mexican dishes. Prices for a substantial meal can range from $5 to $15 per person. Budget-conscious travelers should also visit local markets, where freshly prepared food provides the opportunity to try regional specialties without high costs. Although upscale restaurants offer diverse menus, smaller establishments ensure a more affordable and locally immersive dining experience, allowing visitors to enjoy the region’s flavors while keeping expenses in check.
Is there a specific time of year when Cancun is best visited by travelers from Chicago Midway Airport?
Yes, Cancun is especially appealing during the dry season, which runs from December to April. This period offers pleasant weather and lower humidity levels, ideal for beach outings and exploring outdoor attractions. Although it is the peak tourist season, with possible higher rates, early planning can secure better deals. Travelers from Chicago Midway Airport might also consider the shoulder months of November and May, which offer a balance between favorable weather and fewer crowds, ensuring a more relaxed experience.
What are the customs requirements for travelers flying from Chicago Midway Airport to Cancun?
Customs requirements for travelers flying between these cities include presenting a valid passport and ensuring that necessary travel documents, like a visa if required, are up to date. While U.S. citizens generally don’t need a visa for short visits, it’s essential to complete an immigration form upon arrival in Cancun. Additionally, declare any items that exceed duty-free limits. It is advisable to check both U.S. Customs and Cancun’s entry regulations before departure, as rules may change and might affect your travel preparations.
Are there any seasonal events in Cancun that travelers from Chicago Midway Airport should not miss?
Yes, Cancun plays host to several seasonal events that enhance its cultural landscape. Key events include the Cancun Jazz Festival, various beach parties, and vibrant local fiestas celebrating national holidays. The spring and winter months often feature outdoor music festivals and art exhibitions that highlight regional art and traditions. Travelers can expect event costs to vary from free community events to ticketed gatherings ranging from $20 to $50. Scheduling your visit around these dates can provide a rich, immersive cultural experience.
What are the best shopping areas in Cancun for travelers from Chicago Midway Airport?
One of the prime shopping spots in Cancun is the La Isla Shopping Village, which offers a mix of upscale boutiques and local artisan shops. Mercado 28 is another great area, renowned for its selection of handmade crafts and souvenirs at reasonable prices. Ranging from small vendors to larger retail outlets, these areas provide diverse options with prices typically varying from $10 to $100 per item. Both shopping areas deliver a vibrant experience that allows visitors to take a piece of local culture home.
What health precautions should travelers from Chicago Midway Airport take before visiting Cancun?
Travelers should consider common health precautions before heading to Cancun, such as checking that routine vaccinations are up to date. It’s wise to consult a travel health clinic regarding recommended vaccinations. Additionally, drink bottled water to avoid gastrointestinal issues and protect against sun exposure by using sunscreen, hats, and sunglasses. Over-the-counter medications and a basic first-aid kit are also recommended. Being prepared with travel insurance that covers health emergencies can further secure your overall travel well-being.
What unique cultural experiences can travelers from Chicago Midway Airport enjoy in Cancun?
Cancun offers immersive cultural experiences that enrich any visit. Travelers can join local cooking classes to learn traditional Mexican recipes or attend art and craft workshops to explore Mayan-inspired arts. Visits to nearby archaeological sites provide historical insights into ancient civilizations, while local festivals showcase traditional dance and music. Culinary tours, street food demonstrations, and interactions with local artisans deepen cultural understanding. Engage with local communities through guided tours, ensuring an authentic insight into the rich history and modern vibrancy of the region.
What are the best car rental options in Cancun for travelers from Chicago Midway Airport?
Cancun offers a range of reliable car rental services suitable for diverse travel needs. Major companies provide vehicles with prices ranging from $30 to $70 per day based on car type and season. Local rental agencies may offer competitive rates and flexible plans. It’s advisable to choose options that include comprehensive insurance coverage and roadside assistance. Customers should compare reviews and rates online before booking. Renting a car gives the freedom to explore areas outside the main tourist zones, making it a practical choice for adventurous visitors.
Are there any special airport amenities in Cancun for travelers arriving from Chicago Midway Airport?
Yes, Cancun International Airport provides several amenities to enhance the travel experience. The airport offers modern lounges, duty-free shops catering to luxury and local products, and a variety of dining options ranging from quick bites to sit-down restaurants. Other facilities include free Wi-Fi, currency exchange services, and informational kiosks to assist in local travel planning. For heightened comfort, VIP services and expedited security lanes are available at additional costs. These features ensure travelers have a convenient and pleasant arrival experience.

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