5 days in Illinois & Cancun Itinerary

5 days in Illinois & Cancun Itinerary

Created using Inspirock trip planner

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1
Chicago, United States
— 2 nights
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2
Cancun, Mexico
— 2 nights
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Chicago, United States

— 2 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, and nightlife. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, shop like a local with Chicago Cultural Center, get a new perspective on nature at Field Museum, and take in panoramic vistas at 360 Chicago Observation Deck.

For photos, traveler tips, where to stay, and tourist information, read our Chicago road trip site.

New York City to Chicago is an approximately 4-hour flight. You can also drive; or take a bus. You'll gain 1 hour traveling from New York City to Chicago due to the time zone difference. Traveling from New York City in April, you can expect nighttime temperatures to be a bit cooler in Chicago, with lows of 40°F. Finish your sightseeing early on the 1st (Sat) so you can fly to Cancun.

Things to do in Chicago

Museums · Childrens Museums · Parks · Zoos & Aquariums
Find places to stay Apr 29 — May 1:

Cancun, Mexico

— 2 nights
Few destinations in Mexico dazzle visitors quite like Cancun, a modern resort town filled with glitzy hotels sitting on picturesque and well-developed Caribbean beaches.
On the 2nd (Sun), browse the different shops at La Isla Shopping Village and then stroll through Playa Delfines. Keep things going the next day: don't miss a visit to El Parque de las Palapas and then fulfill a lifelong dream with a swim-with-the-dolphins experience.

To find more things to do, ratings, and more tourist information, read Cancun trip itinerary builder website.

You can fly from Chicago to Cancun in 7 hours. Alternatively, you can drive; or do a combination of train and bus. You'll lose 1 hour traveling from Chicago to Cancun due to the time zone difference. Traveling from Chicago in May, expect nights in Cancun to be warmer, around 75°F, while days are somewhat warmer, around 86°F. Finish your sightseeing early on the 3rd (Mon) so you can fly back home.

Things to do in Cancun

Outdoors · Shopping · Beaches · Parks
Find places to stay May 1 — 3:

Illinois travel guide

4.4
Observation Decks · Parks · Art Museums
The Prairie State
The most populous state in the country's Midwest region, Illinois features a diverse landscape that includes both the enormous urban sprawl of Chicago and flat central plains, devoted almost entirely to farmland. With a great selection of things to do, Chicago is the state's centerpiece, featuring world-famous architecture and renowned museums. Farther away from this giant urban center, you can explore historical landmarks dedicated to local heroes Abraham Lincoln and Ernest Hemingway. The state also includes a prehistoric Native American site, one of only 20 World Heritage Sites in the United States, a unique feature well-worth adding to your itinerary.