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Flight Deals from Cancun to Chicago Midway Airport from $177

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Stops

  • Up to 1 stop
    $325

Airlines

  • Aeromexico
    $325
  • Delta Air Lines
    $325
  • Frontier Airlines
    $497

Cabin Class

  • Economy
    $325

Departure Airports

  • Cancún International Airport
    $325

Arrival Airports

  • Chicago Midway Airport
    $325

Layover Airports

  • Dallas Fort Worth International Airport
    $507
  • Denver International Airport
    $507
  • Hartsfield Jackson Atlanta International Airport
    $325
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $325

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Delta Air Lines Logo
Delta Air Lines

07/16/25

CUN
10h 41m
ATL

07/16/25

MDW
Delta Air Lines Logo
Delta Air Lines

07/30/25

MDW
5h 25m
ATL

07/30/25

CUN
$325
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

07/23/25

CUN
10h 41m
ATL

07/23/25

MDW
Aeromexico Logo
Aeromexico

07/31/25

MDW
7h 1m
MSP

07/31/25

CUN
$325
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

07/16/25

CUN
10h 41m
ATL

07/16/25

MDW
Aeromexico Logo
Aeromexico

07/30/25

MDW
5h 25m
ATL

07/30/25

CUN
$325
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

08/03/25

CUN
7h 41m
ATL

08/03/25

MDW
Aeromexico Logo
Aeromexico

08/17/25

MDW
6h 45m
ATL

08/17/25

CUN
$381
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

08/04/25

CUN
9h 28m
ATL

08/04/25

MDW
Frontier Airlines Logo
Frontier Airlines

08/18/25

MDW
6h 7m
ATL

08/18/25

CUN
$497
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

08/03/25

CUN
9h 28m
ATL

08/03/25

MDW
Frontier Airlines Logo
Frontier Airlines

08/17/25

MDW
6h 7m
ATL

08/17/25

CUN
$497
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/27/25

CUN
20h 16m
DEN

07/28/25

MDW
Frontier Airlines Logo
Frontier Airlines

08/10/25

MDW
6h 7m
ATL

08/10/25

CUN
$507
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/22/25

CUN
20h 51m
ATL

07/23/25

MDW
Frontier Airlines Logo
Frontier Airlines

08/05/25

MDW
15h 35m
DFW

08/06/25

CUN
$507
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/20/25

CUN
9h 28m
ATL

07/20/25

MDW
Frontier Airlines Logo
Frontier Airlines

08/03/25

MDW
6h 7m
ATL

08/03/25

CUN
$518
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/30/25

CUN
29h 29m
DEN

07/31/25

MDW
Frontier Airlines Logo
Frontier Airlines

08/13/25

MDW
24h 48m
ATL

08/14/25

CUN
$538
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/16/25

CUN
23h 58m
ATL

07/17/25

MDW
Frontier Airlines Logo
Frontier Airlines

07/30/25

MDW
24h 48m
ATL

07/31/25

CUN
$538
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

08/04/25

CUN
18h 34m
MSP

08/05/25

MDW
Delta Air Lines Logo
Delta Air Lines

08/18/25

MDW
6h 53m
ATL

08/18/25

CUN
$541
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

08/05/25

CUN
9h 6m
ATL

08/05/25

MDW
Aeromexico Logo
Aeromexico

08/19/25

MDW
8h 8m
ATL

08/19/25

CUN
$554
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

08/05/25

CUN
9h 6m
ATL

08/05/25

MDW
Delta Air Lines Logo
Delta Air Lines

08/19/25

MDW
6h 53m
ATL

08/19/25

CUN
$554
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

08/07/25

CUN
10h 2m
ATL

08/07/25

MDW
Aeromexico Logo
Aeromexico

08/21/25

MDW
9h 23m
ATL

08/21/25

CUN
$585
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

08/09/25

CUN
7h 41m
ATL

08/09/25

MDW
Delta Air Lines Logo
Delta Air Lines

08/23/25

MDW
8h 8m
ATL

08/23/25

CUN
$635
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

07/20/25

CUN
7h 37m
ATL

07/20/25

MDW
Aeromexico Logo
Aeromexico

08/03/25

MDW
6h 50m
ATL

08/03/25

CUN
$682
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

07/27/25

CUN
18h 34m
MSP

07/28/25

MDW
Delta Air Lines Logo
Delta Air Lines

08/10/25

MDW
8h 25m
ATL

08/10/25

CUN
$790
Free cancellation within 83 hours of booking

Top Deals on flights from Cancun to Chicago Midway Airport

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

Aeromexico Logo
Aeromexico

Jun 11

CUN
9h 10m
ATL

Jun 11

MDW

as low as

$177

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

Delta Air Lines Logo
Delta Air Lines

May 2

CUN
6h 12m
ATL

May 2

MDW

as low as

$177

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

Delta Air Lines Logo
Delta Air Lines

Jul 2

CUN
8h 46m
ATL
DTW

Jul 2

MDW

as low as

$182

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

Frontier Airlines Logo
Frontier Airlines

Jul 11

CUN
11h 16m
PHL

Jul 11

MDW

as low as

$183

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

Frontier Airlines Logo
Frontier Airlines

Aug 13

CUN
29h 29m
DEN

Aug 14

MDW

as low as

$194

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

Delta Air Lines Logo
Delta Air Lines

Jun 16

CUN
15h 42m
MEX
ATL

Jun 16

MDW

as low as

$209

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

 Logo

Jul 30

CUN
3h 35m
Direct

Jul 30

MDW

as low as

$233

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

Frontier Airlines Logo
Frontier Airlines

May 30

CUN
26h 59m
DFW

May 31

MDW

as low as

$241

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

Frontier Airlines Logo
Frontier Airlines

May 31

CUN
10h 57m
MCO

May 31

MDW

as low as

$243

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

 Logo

Jul 30

CUN
11h 20m
BWI

Jul 30

MDW

as low as

$243

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

 Logo

May 12

CUN
9h 43m
ATL

May 12

MDW

as low as

$301

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

 Logo

Jul 30

CUN
11h 16m
GDL

Jul 30

MDW

as low as

$361

Frequently Asked Questions

What is the typical flight duration from Cancun to Chicago Midway Airport?
The typical flight duration from Cancun to Chicago Midway Airport ranges between 4 to 5 hours for direct flights, while flights with one stop might extend up to 7 to 8 hours depending on layover timings. Travelers should consider potential weather delays and check updated schedules before departure. It’s advisable to plan extra time for boarding and security procedures. When traveling from Cancun to Chicago, planning ahead will help ensure a smooth connection between the flight and subsequent ground transfers at the destination.
Are there any direct flights from Cancun to Chicago Midway Airport?
Yes, there are direct flights from Cancun to Chicago Midway Airport. However, availability depends on seasonal schedules and airline operations, meaning options might be more frequent during high travel demand periods. It is recommended to verify timings as direct flights typically range from 4 to 5 hours and may have limited departures compared to connecting flights. Travelers from Cancun heading to Chicago should compare available flights and consider booking early to secure the best travel times and potentially lower fares.
What are the best transportation options from Chicago Midway Airport to downtown Chicago?
The best transportation options from Chicago Midway Airport to downtown Chicago include a variety of choices such as taxis, ride-sharing services, and public transit. Taxis usually cost between $20 to $35 while ride-sharing fares can vary based on demand, often falling within a similar range. Alternatively, the CTA Orange Line provides a budget-friendly option with fares ranging from $3 to $5 and a travel time of 20 to 30 minutes. Travelers can also check bus routes for additional cost-effective alternatives when moving from the airport to central Chicago.
What are the must-see attractions in Chicago for travelers arriving from Cancun?
For travelers arriving from Cancun, Chicago offers a wealth of attractions that combine cultural, architectural, and recreational delights. Notable landmarks include Millennium Park with its iconic Bean sculpture, Navy Pier with its rides and lake views, the Art Institute of Chicago for art enthusiasts, and the Willis Tower Skydeck for panoramic city vistas. Exploring neighborhoods like the Chicago Riverwalk, or taking an architecture boat tour, can enrich your experience. These diverse attractions ensure a memorable visit filled with unique and lively urban experiences.
Which local dishes should travelers from Cancun try when visiting Chicago?
Travelers from Cancun visiting Chicago should definitely sample local culinary specialties that reflect the city’s rich food culture. Iconic dishes include Chicago-style deep-dish pizza, known for its hearty crust and robust toppings, and the Chicago-style hot dog, which comes loaded with flavorful toppings without ketchup. Additionally, try the Italian beef sandwich for a taste of local deli cuisine. Many eateries offer versions of these dishes at prices typically ranging from $10 to $25, allowing for a diverse sampling of authentic, hearty Midwestern cuisine.
Are there any family-friendly activities in Chicago for visitors from Cancun?
Yes, Chicago offers several family-friendly activities ideal for visitors from Cancun. Families can explore the Lincoln Park Zoo, which is free of charge, and the interactive exhibits at the Chicago Children's Museum located at Navy Pier. Other great options include visiting the Field Museum and the Shedd Aquarium, with entry fees typically ranging from $20 to $40 per person. These attractions provide educational yet fun experiences, ensuring that children and adults alike enjoy the diverse cultural and recreational offerings in the city.
What are the best budget-friendly hotels in Chicago for travelers from Cancun?
Budget-conscious visitors from Cancun can find a variety of affordable hotel options in Chicago. Areas such as the Loop, South Loop, or near public transportation hubs often feature hotels with rates ranging from $100 to $200 per night. Chains like Holiday Inn Express, or locally owned boutique hotels, offer comfortable accommodations, complimentary breakfast, and proximity to popular attractions. Booking in advance and comparing prices online can lead to additional savings. Always check traveler reviews to ensure quality and safety while enjoying a comfortable stay within your budget.
What are the customs requirements for travelers flying from Cancun to Chicago Midway Airport?
Travelers flying from Cancun to Chicago Midway Airport must comply with US customs and immigration requirements. This typically involves presenting a valid passport along with a suitable visa or an ESTA approval for eligible travelers. Be prepared to complete customs declaration forms and declare any items as required by the US Customs and Border Protection. It is advisable to check updated guidelines on the official CBP website prior to travel, as requirements may change. Visitors should also allow extra time at the airport to complete all necessary customs and security procedures upon arrival.
Is there a specific time of year when Chicago is best visited by travelers from Cancun?
Yes, the best times to visit Chicago for those traveling from Cancun are during late spring, from May to June, and early fall, from September to October. These seasons offer mild temperatures, typically ranging from 60°F to 75°F, and lower humidity compared to the summer months. Additionally, fewer tourists during these times can result in shorter wait times at attractions and potentially better deals on accommodations. Travelers should consider these periods for comfortable sightseeing along with enjoying outdoor festivals and scenic views of the city's iconic architecture.
What are the top shopping districts in Chicago for travelers arriving from Cancun?
Chicago boasts several vibrant shopping districts that appeal to visitors from Cancun looking for diverse retail experiences. The Magnificent Mile, a bustling stretch of Michigan Avenue, offers high-end boutiques, designer brands, and flagship stores. State Street provides more accessible shopping experiences with department stores and unique local shops. Additionally, neighborhoods such as Wicker Park offer indie boutiques and vintage finds. Prices in these districts vary widely, from affordable local labels to upscale designer goods, ensuring that every budget is catered to while exploring the city’s dynamic shopping scene.
What health precautions should travelers from Cancun consider before visiting Chicago?
Travelers from Cancun should consider several health precautions when planning a trip to Chicago. It is wise to check that routine vaccinations are up-to-date and consider a seasonal flu shot, especially during peak flu season. Given potential temperature swings, packing appropriate clothing and allergy medications is advisable. Additionally, verifying current COVID-19 health guidelines and local advisories can enhance safety. Consider travel insurance covering medical emergencies, which generally ranges from $5 to $20 per day. Carrying a basic first aid kit and ensuring that food allergies are managed can help ensure a healthy visit to the city.
Are there any seasonal events in Chicago that travelers from Cancun should not miss?
Yes, there are several seasonal events in Chicago that travelers from Cancun should not miss. In the summer months, events like the Taste of Chicago food festival and the Chicago Air and Water Show provide exciting outdoor entertainment and cultural exposure. The autumn season features festive harvest fairs and theater festivals, while the winter brings holiday markets and ice-skating rinks set against scenic backdrops. Ticket prices generally range from $20 to $100 depending on the event. Checking local event calendars ahead of time can ensure you experience the most celebrated local festivities during your visit.
What unique airport amenities are available at Chicago Midway Airport for travelers arriving from Cancun?
Chicago Midway Airport provides several unique amenities to enhance the traveler’s experience upon arrival from Cancun. Passengers can enjoy free Wi-Fi, a variety of dining establishments offering meals in the $10 to $30 range, and retail shops featuring local and national brands. The airport also features mobile charging stations and comfortable lounges for relaxation. Additionally, tasteful art installations and clean, well-maintained facilities provide a pleasant environment even during short layovers. These thoughtful conveniences help streamline your transition from the flight to your onward journey in the city.
What are the best solo travel activities in Chicago for travelers arriving from Cancun?
Solo travelers arriving from Cancun will find plenty of engaging activities in Chicago. Consider joining cultural walking tours to explore rich neighborhoods, taking a river cruise to appreciate the city’s stunning architecture, or visiting renowned museums such as the Art Institute or the Museum of Contemporary Art. Additionally, local food tours offer a unique insight into the regional cuisine. Many of these activities cost between $15 and $30, providing affordable opportunities for self-guided exploration. The city’s well-connected public transit further enables solo adventurers to navigate comfortably and safely throughout Chicago.
How does public transportation in Chicago compare for travelers arriving from Cancun?
Public transportation in Chicago is efficient and affordable for travelers arriving from Cancun. The city’s CTA network, comprising buses and trains, offers fares ranging from $3 to $5 per ride, with daily and multi-day passes available for frequent use. This extensive system makes it convenient to reach major landmarks, shopping districts, and attractions from the airport. Compared to other major cities, Chicago’s transit is well-regarded for its punctuality and easy-to-follow route maps. This accessible system allows visitors to explore the city without relying heavily on taxis or ride-shares, thereby balancing convenience and cost-effectiveness.

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