Located on the shore of Lake Michigan, Chicago offers a variety of attractions to make a stunning city break. With 24 beaches, you will be spoilt for choice to experience Chicago’s aquatic charms. Visitors to the Navy Pier can enjoy top-class entertainment including amusements and fireworks, whilst a little further afield, River North offers fresh air and the chance to sample galleries and quaint gift-shops.

If you have a head for heights, the 103rd floor Skydeck at the Willis Tower will provide you with a stunning panorama of the city to enjoy, whilst the foodies will can sample Chicago’s famous Italian-American cuisine to their heart’s content at Gino’s East Pizza. The John Hancock Observatory offers an unforgettable dining experience for romantics, whilst there are shopping opportunities aplenty on the Magnificent Mile. Meanwhile, if you want to party the night away, the Rush & Division district will enable you to try out your dancing shoes. With so many options, a break in the Windy City will blow you away!


What you’ll love most about Chicago

  • Shop and dine along the Magnificent Mile, Chicago’s premier shopping district. Explore upscale boutiques, department stores, and luxury retailers, and enjoy fine dining, casual eateries, and vibrant nightlife options
  • Discover the iconic Millennium Park, home to the famous Cloud Gate sculpture, also known as “The Bean.” Take a selfie with the reflective sculpture, stroll through the lush gardens, and enjoy outdoor concerts and art installations in the park
  • Experience family-friendly fun at Navy Pier, a historic landmark and entertainment complex along Lake Michigan. Ride the Ferris wheel for panoramic views of the city skyline, enjoy carnival rides and games, and explore attractions like the Chicago Children’s Museum and Chicago Shakespeare Theatre
  • Immerse yourself in art at the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Explore its vast collection of over 300,000 artworks, including masterpieces by artists like Picasso, Monet, and Van Gogh
  • Take a leisurely stroll along the Chicago Riverwalk, a scenic promenade lined with restaurants, bars, and public art installations. Enjoy waterfront dining, boat tours, and architectural cruises, and marvel at the city’s iconic skyline reflected in the river
  • Soar to new heights at the Willis Tower Skydeck, offering panoramic views from the tallest building in the Western Hemisphere. Step out onto “The Ledge,” a glass-floored observation deck, and experience the thrill of standing 1,353 feet above the city streets
  • Chicago architecture boat tour - Illinois Office of Tourism/Jason Lindsey

  • Chicago beach - Illinois Office of Tourism

  • Downtown Chicago

  • Chicago Cubs Wrigley Field - Illinois Office of Tourism

  • Chicago water taxi - Illinois Office of Tourism/Dice Sales

  • Osaka Garden, Chicago - Illinois Office of Tourism

  • The Bean at Millenium Park - Illinois Office of Tourism

  • Odyssey on the Chicago River - Illinois Office of Tourism

  • Chicago skyline and Navy Pier - Illinois Office of Tourism

  • Chicago street mural on Pilsen - Illinois Office of Tourism

  • Chicago Riverwalk on a summer's evening - Illinois Office of Tourism

  • Shoreline sightseeing firework cruise - Illinois Office of Tourism

Average temperature

Information below is based on average highest temperature for each month.

  • -1℃
  • 1℃
  • 8℃
  • 15℃
  • 21℃
  • 27℃
  • 29℃
  • 28℃
  • 24℃
  • 17℃
  • 9℃
  • 2℃
  • 8
  • 7
  • 13
  • 12
  • 17
  • 12
  • 12
  • 13
  • 10
  • 13
  • 14
  • 9

Information above is based on the average number of days which experience some form of rainfall for each month.


When to Visit

Below gives you information and a rating of the best time of year to visit.













Our Ratings

  • Most Recommended
  • Recommended
  • Highly Recommended
  • Not Recommended

Where to book

American Sky offers luxury tailor-made tours and holidays specialising in providing expert travel advice and exceptional unhurried customer service. With a wealth of experience we will find the perfect trip for you.

Visit website for more info

More info

eShores specialises in tailor-made multi-centre holidays, seamlessly blending multiple destinations into one trip. Explore the beauty of Thailand, island-hop the Greek islands, or embark on an epic American road trip – anything is possible. With consultants averaging 15 years’ experience, your dream holiday is in expert hands, so you can relax and enjoy the adventure!

Visit website for more info

More info

“We’re not your ordinary travel agency. We’re a community of travellers.
WeRoad was born to connect people, cultures and stories through that magical activity that we call ‘travelling’. We group people together and send them to live incredible adventures around the globe.”

Visit website for more info

More info

Have you considered...

Nestled in the heart of the United States to the west of Chicago and the Great Lakes, Minnesota captivates with its diverse landscapes, from the urban sophistication of the Twin Cities, Minneapolis and St. Paul, to the pristine wilderness that earned it the moniker “Land of 10,000 Lakes.”


Top Holiday Offers

We’ve hand-picked a range of enticing offers to incredible destinations. If you want value for money on your next trip, start by reviewing our dedicated Top Holiday Offers page.

Top Offers