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Flight Deals from Cancun to Chicago from $120

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Stops

  • Nonstop
    from $233
  • Up to 1 stop
    $308

Airlines

  • Aeromexico
    $325
  • American Airlines
    $336
  • Delta Air Lines
    $325
  • Frontier Airlines
    $233
  • JetBlue
    $456
  • Spirit Airlines
    $302
  • United Airlines
    $308

Cabin Class

  • Economy
    $233

Departure Airports

  • Cancún International Airport
    $233

Arrival Airports

  • Chicago Midway Airport
    $325
  • Chicago O Hare Airport
    $233

Layover Airports

  • Charlotte Douglas International Airport
    $366
  • Dallas Fort Worth International Airport
    $336
  • Denver International Airport
    $355
  • Detroit Metropolitan Airport
    $325
  • Fort Lauderdale Hollywood International Airport
    $311
  • General Edward Lawrence Logan International Airport
    $456
  • George Bush Intercontinental Houston Airport
    $308
  • Hartsfield Jackson Atlanta International Airport
    $325
  • Licenciado Benito Juarez International Airport
    $377
  • Miami International Airport
    $336
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $325
  • New York John F Kennedy Airport
    $456
  • Orlando International Airport
    $354

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Frontier Airlines Logo
Frontier Airlines

07/30/25

CUN
4h 1m
Direct

07/30/25

ORD
Frontier Airlines Logo
Frontier Airlines

08/13/25

ORD
3h 55m
Direct

08/13/25

CUN
$233
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

07/31/25

CUN
4h 3m
Direct

07/31/25

ORD
Spirit Airlines Logo
Spirit Airlines

08/05/25

ORD
3h 31m
Direct

08/05/25

CUN
$302
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

07/15/25

CUN
4h 3m
Direct

07/15/25

ORD
Spirit Airlines Logo
Spirit Airlines

07/29/25

ORD
3h 31m
Direct

07/29/25

CUN
$302
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/29/25

CUN
6h 51m
IAH

07/29/25

ORD
United Airlines Logo
United Airlines

08/12/25

ORD
3h 46m
Direct

08/12/25

CUN
$308
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

07/29/25

CUN
4h 3m
Direct

07/29/25

ORD
Spirit Airlines Logo
Spirit Airlines

08/12/25

ORD
6h 28m
FLL

08/12/25

CUN
$311
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

07/29/25

CUN
7h 4m
ATL

07/29/25

ORD
Delta Air Lines Logo
Delta Air Lines

08/12/25

ORD
6h 58m
ATL

08/12/25

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

08/02/25

CUN
6h 34m
ATL

08/02/25

ORD
Aeromexico Logo
Aeromexico

08/08/25

ORD
7h 1m
MSP

08/08/25

CUN
$325
Free cancellation within 83 hours of booking
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

07/30/25

CUN
7h 49m
ATL

07/30/25

ORD
Aeromexico Logo
Aeromexico

08/13/25

ORD
6h 58m
ATL

08/13/25

CUN
$325
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

07/15/25

CUN
8h 54m
ATL

07/15/25

ORD
Delta Air Lines Logo
Delta Air Lines

07/29/25

ORD
5h 50m
DTW

07/29/25

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
United Airlines Logo
United Airlines

07/30/25

CUN
4h 2m
Direct

07/30/25

ORD
United Airlines Logo
United Airlines

08/13/25

ORD
3h 53m
Direct

08/13/25

CUN
$326
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/29/25

CUN
6h 53m
DFW

07/30/25

ORD
American Airlines Logo
American Airlines

08/12/25

ORD
3h 40m
Direct

08/12/25

CUN
$336
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

08/06/25

CUN
7h 56m
MIA

08/06/25

ORD
American Airlines Logo
American Airlines

08/20/25

ORD
3h 40m
Direct

08/20/25

CUN
$336
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

08/06/25

CUN
6h 51m
IAH

08/06/25

ORD
United Airlines Logo
United Airlines

08/20/25

ORD
3h 45m
Direct

08/20/25

CUN
$341
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

07/22/25

CUN
7h 35m
MCO

07/22/25

ORD
Spirit Airlines Logo
Spirit Airlines

08/05/25

ORD
3h 31m
Direct

08/05/25

CUN
$354
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

07/15/25

CUN
4h 3m
Direct

07/15/25

ORD
Spirit Airlines Logo
Spirit Airlines

07/29/25

ORD
6h 28m
FLL

07/29/25

CUN
$354
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/28/25

CUN
10h 20m
DEN

07/29/25

ORD
United Airlines Logo
United Airlines

08/11/25

ORD
3h 46m
Direct

08/11/25

CUN
$355
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/30/25

CUN
10h 20m
DEN

07/31/25

ORD
United Airlines Logo
United Airlines

08/13/25

ORD
3h 46m
Direct

08/13/25

CUN
$360
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/29/25

CUN
9h 3m
MIA

07/29/25

ORD
American Airlines Logo
American Airlines

08/12/25

ORD
7h 55m
CLT

08/12/25

CUN
$366
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/22/25

CUN
9h 3m
MIA

07/22/25

ORD
American Airlines Logo
American Airlines

08/05/25

ORD
7h
DFW

08/05/25

CUN
$366
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

08/06/25

CUN
8h 40m
MIA

08/06/25

ORD
American Airlines Logo
American Airlines

08/20/25

ORD
7h 10m
MIA

08/20/25

CUN
$366
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

08/09/25

CUN
8h 15m
MEX

08/09/25

ORD
Aeromexico Logo
Aeromexico

08/18/25

ORD
8h 8m
ATL

08/18/25

CUN
$377
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

07/18/25

CUN
10h 9m
ATL

07/19/25

ORD
Delta Air Lines Logo
Delta Air Lines

08/01/25

ORD
5h 50m
DTW

08/01/25

CUN
$377
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/21/25

CUN
4h 1m
Direct

07/21/25

ORD
Frontier Airlines Logo
Frontier Airlines

08/04/25

ORD
3h 55m
Direct

08/04/25

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

07/21/25

CUN
6h 41m
CLT

07/21/25

ORD
American Airlines Logo
American Airlines

08/04/25

ORD
8h 17m
CLT

08/04/25

CUN
$386
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

08/14/25

CUN
6h 20m
ATL

08/14/25

ORD
Delta Air Lines Logo
Delta Air Lines

08/28/25

ORD
11h 54m
MEX

08/28/25

CUN
$397
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

07/22/25

CUN
7h 35m
MCO

07/22/25

ORD
Spirit Airlines Logo
Spirit Airlines

08/05/25

ORD
6h 28m
FLL

08/05/25

CUN
$407
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

07/15/25

CUN
17h 20m
BOS

07/16/25

ORD
JetBlue Logo
JetBlue

07/29/25

ORD
11h 30m
JFK

07/29/25

CUN
$456
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

07/28/25

CUN
17h 20m
BOS

07/29/25

ORD
JetBlue Logo
JetBlue

08/11/25

ORD
11h 30m
JFK

08/11/25

CUN
$502
Free cancellation within 83 hours of booking

Top Deals on flights from Cancun to Chicago

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

Spirit Airlines Logo
Spirit Airlines

May 9

CUN
3h 57m
Direct

May 9

ORD

as low as

$120

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

Frontier Airlines Logo
Frontier Airlines

May 16

CUN
4h 1m
Direct

May 16

ORD

as low as

$129

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

United Airlines Logo
United Airlines

May 15

CUN
4h 2m
Direct

May 15

ORD

as low as

$136

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

Spirit Airlines Logo
Spirit Airlines

May 9

CUN
10h
IAH

May 9

ORD

as low as

$147

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

Spirit Airlines Logo
Spirit Airlines

May 7

CUN
10h 46m
FLL

May 7

ORD

as low as

$147

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

Spirit Airlines Logo
Spirit Airlines

May 8

CUN
14h 17m
MCO

May 8

ORD

as low as

$147

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

 Logo

Jun 2

CUN
3h 57m
Direct

Jun 2

ORD

as low as

$153

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

American Airlines Logo
American Airlines

Aug 21

CUN
4h
Direct

Aug 21

ORD

as low as

$162

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

Aeromexico Logo
Aeromexico

Jul 31

CUN
10h 9m
ATL

Aug 1

ORD

as low as

$168

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

Delta Air Lines Logo
Delta Air Lines

Jul 19

CUN
11h 42m
MEX

Jul 20

ORD

as low as

$168

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

 Logo

Jul 31

CUN
10h 9m
ATL

Aug 1

ORD

as low as

$173

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

American Airlines Logo
American Airlines

Jul 11

CUN
12h 24m
MIA

Jul 11

ORD

as low as

$177

Frequently Asked Questions

What is the typical flight duration from Cancun to Chicago?
The typical flight duration from Cancun to Chicago usually ranges between 4 to 5 hours for direct flights. However, if you choose a connecting option, the total travel time can extend up to 6 or more hours depending on layover durations. It’s advisable to check schedules when booking as flight durations might slightly vary with weather conditions and air traffic. This information helps plan your travel timing and ensures you allocate sufficient time for transfers or connecting flights when flying between Cancun and Chicago.
Are there any direct flights from Cancun to Chicago?
Yes, there are direct flights from Cancun to Chicago available, especially during peak travel seasons. Direct options typically help save time as you can avoid long layovers found in connecting flights. However, the frequency and availability of direct flights can vary based on the airline’s schedule and season. Be sure to check for promotions and flight timings that suit your travel plans. This allows you to conveniently travel between Cancun and Chicago while minimizing the hassle of multiple stops.
What are the best transportation options from Chicago airport to downtown or popular tourist attractions?
Travelers arriving at Chicago’s airport have several reliable transportation options. The CTA’s Blue Line offers a cost-effective way, generally costing between $5 and $10 per ride, directly connecting to downtown. Additionally, taxis and rideshare services provide convenience and take approximately 20 to 45 minutes depending on traffic, with fares ranging from $30 to $50. For those preferring private transfers, shuttle services operate on scheduled departures. These options ensure a smooth transition from the airport to major attractions in Chicago.
What are the must-see attractions in Chicago for travelers arriving from Cancun?
Travelers coming from Cancun should not miss Chicago’s top attractions. Iconic landmarks such as Millennium Park, the Art Institute of Chicago, and the Willis Tower Skydeck are must-visits, offering a mix of art, architecture, and panoramic city views. Navy Pier also provides family-friendly entertainment and scenic lake views. Many attractions are centrally located, making them easily accessible by public transit or taxi. Detailed planning helps maximize your sightseeing experience when transitioning from Cancun to the dynamic urban environment of Chicago.
Which local dishes should travelers from Cancun try when visiting Chicago?
Travelers from Cancun should explore Chicago’s culinary scene by trying its signature dishes. Start with the renowned Chicago deep-dish pizza, which comes with a rich tomato sauce and hearty toppings. Additionally, the classic Chicago-style hot dog and Italian beef sandwich offer local twists on traditional flavors. Prices generally range from $10 to $25 per meal depending on restaurant choice. These dishes not only highlight the city’s diverse food culture but also provide a delicious contrast to the cuisine typically enjoyed in Cancun.
What are the best family-friendly activities in Chicago for visitors from Cancun?
Chicago offers a variety of family-friendly activities ideal for visitors from Cancun. Highlights include visiting the Shedd Aquarium, where exhibits range between $30 and $50 per ticket, and exploring the Field Museum which engages both adults and children with educational exhibits. Families may also enjoy the interactive exhibits at the Museum of Science and Industry or a day at the Lincoln Park Zoo, which is generally free. These attractions ensure that visitors of all ages have enjoyable, memorable experiences during their stay in Chicago.
Are there any cultural festivals in Chicago that travelers from Cancun should not miss?
Yes, Chicago hosts a vibrant array of cultural festivals that travelers from Cancun should consider attending. Events such as the Chicago Blues Festival, Taste of Chicago, and various neighborhood cultural celebrations highlight the city’s rich artistic and culinary traditions. These festivals usually take place during the warmer months when the weather is pleasant, with ticket prices or participation fees often ranging from free entry to about $30. Participating in these events provides a great way to experience Chicago’s diverse culture and community spirit.
What are the most affordable dining options in Chicago for travelers from Cancun?
Chicago offers several affordable dining options to accommodate travelers from Cancun on a budget. Local diners, street food vendors, and food trucks serve hearty meals such as deep-dish pizza slices or Chicago-style hot dogs, with prices generally ranging from $7 to $15. Neighborhood eateries in areas like Pilsen or Logan Square can also provide excellent dining experiences without the high costs of downtown restaurants. Exploring these options allows you to savor authentic local flavors while keeping your travel budget in check.
What are the best shopping areas in Chicago for souvenirs that travelers from Cancun should explore?
Shoppers visiting Chicago can explore several popular areas to find unique souvenirs. The Magnificent Mile offers a mix of high-end boutiques and local souvenir shops, while State Street provides an atmosphere rich in local flavor with prices generally ranging from $10 to $50 per item. Neighborhood markets and specialty stores often highlight regional crafts and authentic Chicago memorabilia. These spots offer travelers from Cancun an opportunity to take home distinctive keepsakes that capture the spirit and cultural vibrancy of the city.
What health precautions should travelers from Cancun take before flying to Chicago?
Travelers should consider a few health precautions before flying from Cancun to Chicago. It is recommended to have up-to-date vaccinations, including routine immunizations, and to consult a travel health clinic for advice on any additional shots like influenza, especially during seasonal peaks. Carrying a basic medical kit and travel insurance with health coverage is also advised, with costs potentially ranging from $50 to $150 depending on coverage. This proactive approach helps ensure a safe, healthy journey between your departure city and Chicago.
Is there a specific time of year when Chicago is best visited by travelers from Cancun?
Yes, Chicago is often best visited during late spring (May to June) or early fall (September to October), when the weather is mild and comfortable. During these periods, travelers from Cancun can enjoy pleasant temperatures while exploring outdoor attractions and festivals, and avoid the extreme cold of winter or the high heat of summer. Additionally, these shoulder seasons usually offer less crowded tourist sites and more favorable accommodation rates, ensuring a more relaxed and budget-friendly experience in Chicago.
What are the best seating options for families traveling from Cancun to Chicago?
When booking flights from Cancun to Chicago, families should consider selecting seating options that enhance comfort and convenience. Airlines often offer bulkhead or exit row seats which provide extra legroom and space, making them ideal for family travel. Options can range from standard economy seats priced similarly to regular fare to premium economy options with a slight price increase, generally between an extra $20 to $50 per ticket. Reserving seats in advance and informing the airline of family needs can help secure an arrangement that caters to both comfort and accessibility.
Are there any airport services in Chicago for travelers with special needs arriving from Cancun?
Yes, Chicago’s airport offers a comprehensive range of services for travelers with special needs. These include wheelchair assistance, accessible restrooms, and designated help points throughout the terminal. Special services also extend to priority boarding and dedicated check-in counters, generally available at no extra charge when requested in advance. It is advisable to contact the airport or your airline before departure to ensure these services are arranged, ensuring a comfortable and hassle-free arrival for travelers coming from Cancun to Chicago.
What unique airport amenities can travelers expect at Chicago for their arrival from Cancun?
Travelers arriving at Chicago’s airport can expect a variety of unique amenities that enhance the travel experience. Many terminals boast modern lounges, free Wi-Fi, art installations, and a range of dining options spanning quick bites to full-service restaurants. Family care rooms, charging stations, and retail shops offering local crafts add to the convenience. These amenities, available at no additional cost or within a price range of $10 to $30 for premium services, ensure a smooth transition and a comfortable start to your visit from Cancun to Chicago.
What are the customs requirements for travelers flying from Cancun to Chicago?
Travelers flying from Cancun to Chicago are required to comply with U.S. customs and immigration protocols. This includes presenting a valid passport and completing a customs declaration form upon arrival. Depending on your residency or visa status, additional documentation such as visas or ESTA approval may be necessary. It’s important to declare any items subject to duty and be aware of restrictions on food, plants, or large sums of cash. Preparing these documents in advance ensures a smoother entry process when transitioning from Cancun to Chicago.

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