Chicago

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Weather

Thu

24°C

Fri

24.6°C

Sat

20.2°C

Experiences

  • Art and culture
  • Architecture
  • Food and drink
  • Outdoor activities

Windy City Wonders: A Traveler’s Guide to Chicago

Welcome to Chicago, where the skyline reaches for the heavens, and the spirit of innovation dances through the streets. Stroll along the famed Magnificent Mile, where high-end boutiques and flagship stores offer a shopper’s paradise. Dive into the architectural marvels of the city on a boat tour along the Chicago River, unraveling the stories behind each towering skyscraper. Immerse yourself in art at the renowned Art Institute of Chicago, boasting a collection that spans continents and centuries. And don’t forget to tantalize your taste buds with deep-dish pizza or gourmet cuisine crafted by world-class chefs. Chicago invites you to explore its vibrant energy and endless possibilities.

But amidst the urban hustle, Chicago also offers serene retreats. Lose yourself in the green expanses of Grant Park, where gardens and fountains provide a refreshing escape. Millennium Park beckons with its modern art installations and panoramic views of the skyline. Dive into the city’s rich musical heritage in historic venues, where the echoes of jazz and blues legends still resonate. From the historic charm of Old Town to the breathtaking vistas from Willis Tower, Chicago promises an unforgettable journey through its vibrant tapestry of culture, history, and natural beauty. Join us and uncover the allure of the Windy City.

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Hotel Deals

Best deals in hotels!


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3-Nights stay in New York

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JW Marriott Essex House

New York, NY, USA
Dec 15, 23 to Dec 18, 23


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xx%OFF

3-Nights stay in New York

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JW Marriott Essex House

New York, NY, USA
Dec 15, 23 to Dec 18, 23


Deal
xx%OFF

3-Nights stay in New York

Save xx%





JW Marriott Essex House

New York, NY, USA
Dec 15, 23 to Dec 18, 23


Deal
xx%OFF

3-Nights stay in New York

Save xx%





JW Marriott Essex House

New York, NY, USA
Dec 15, 23 to Dec 18, 23

Activity Deals

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Famous Artists of Manhattan : City Exploration Game

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Dive into the dark history of Daredevils who did not survive, the tragedies and mysteries with a costumed guide on a lantern tour…Read More
2 h 30 mFree Cancellation


Deal
xx%OFF

Famous Artists of Manhattan : City Exploration Game

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Dive into the dark history of Daredevils who did not survive, the tragedies and mysteries with a costumed guide on a lantern tour…Read More
2 h 30 mFree Cancellation


Deal
xx%OFF

Famous Artists of Manhattan : City Exploration Game

Save xx%


Dive into the dark history of Daredevils who did not survive, the tragedies and mysteries with a costumed guide on a lantern tour…Read More
2 h 30 mFree Cancellation


Deal
xx%OFF

Famous Artists of Manhattan : City Exploration Game

Save xx%


Dive into the dark history of Daredevils who did not survive, the tragedies and mysteries with a costumed guide on a lantern tour…Read More
2 h 30 mFree Cancellation

Car Deals

Best deals in cars!


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Economy car for 8 days in New York

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Toyota Corolla or similar

Pickup Location

New York, NY, USA

Dropoff Location

New York, NY, USA

Class

Compact

Pickup Time

Mon 19, 2023, 11:00 am

Dropoff Time

Mon 20, 2023, 11:00 am

04
02
02


Deal
xx%OFF

Economy car for 8 days in New York

Save xx%

Toyota Corolla or similar

Pickup Location

New York, NY, USA

Dropoff Location

New York, NY, USA

Class

Compact

Pickup Time

Mon 19, 2023, 11:00 am

Dropoff Time

Mon 20, 2023, 11:00 am

04
02
02


Deal
xx%OFF

Economy car for 8 days in New York

Save xx%

Toyota Corolla or similar

Pickup Location

New York, NY, USA

Dropoff Location

New York, NY, USA

Class

Compact

Pickup Time

Mon 19, 2023, 11:00 am

Dropoff Time

Mon 20, 2023, 11:00 am

04
02
02


Deal
xx%OFF

Economy car for 8 days in New York

Save xx%

Toyota Corolla or similar

Pickup Location

New York, NY, USA

Dropoff Location

New York, NY, USA

Class

Compact

Pickup Time

Mon 19, 2023, 11:00 am

Dropoff Time

Mon 20, 2023, 11:00 am

04
02
02

Explore Chicago

Chicago’s a breeze to navigate, offering a variety of options to get around depending on your preference.

  • Public Transportation: Chicago’s public transportation system, the CTA (Chicago Transit Authority), is extensive and affordable. The L train (elevated train) is a great way to get around quickly and efficiently. Buses fill in the gaps, reaching most neighborhoods. Get a Ventra card for easy fare payment across CTA trains and buses.
  • Walking: Chicago’s a walkable city, especially downtown. Many top attractions are concentrated within a few miles of each other, so lace up your walking shoes and explore!
  • Biking: Divvy, Chicago’s bike-sharing program, is a great way to get around on two wheels. Stations are located throughout the city, and rentals are affordable.
  • Taxis & Ride Sharing: Taxis are readily available in most areas, and ride-sharing services like Uber and Lyft are also popular options.
  • Hop-On Hop-Off Bus Tours: For a narrated tour with convenient stops at major attractions, consider a hop-on hop-off bus tour.

Chicago offers something for everyone, but the best time to visit depends on what you prioritize.

For warm weather, long days, and vibrant festivals, summer (June-August) is ideal. However, this peak season comes with crowds and higher prices.

Shoulder seasons (April-May and September-October) provide a happy medium. Enjoy pleasant weather, smaller crowds, and more affordable travel compared to peak season. Spring can be rainy, but fall boasts beautiful foliage.

Winter (December-February) transforms Chicago into a winter wonderland. Embrace the magic of the city with festive decorations, lower hotel rates, and activities like ice skating. However, be prepared for cold and snowy weather.

Consider these additional factors:

  • Events: Research festivals, concerts, sporting events, or art fairs that interest you and plan your trip around them.
  • Prices: Budget travelers will find the best deals during shoulder seasons, while peak season comes with a premium price tag.
  • Crowds: Chicago is always popular, but expect larger crowds, particularly in the summer months.

Chicago, the Windy City, is a metropolis with a rich history, stunning architecture, and a vibrant culture. Here are some of the things to do in Chicago:

  • Catch a free concert or movie: Chicago has a thriving arts scene, and there are often free events happening throughout the city. Check out a free concert in Millennium Park, or catch a movie under the stars at one of Chicago’s many outdoor theaters.
  • Go on a bike ride or walk along the lakefront: Chicago’s lakefront is a beautiful place to spend a day. Rent a bike and cruise along the lakefront path, or take a walk and enjoy the views of the city skyline and Lake Michigan.
  • Browse the farmers markets: Chicago has a number of farmers markets that are great places to find fresh, local produce. You can also find flowers, baked goods, and other locally-made products.
  • Catch a game: Chicago is home to a number of professional sports teams, including the Cubs, the White Sox, the Bears, the Blackhawks, and the Bulls. Take in a game and experience the excitement of Chicago sports.