Discover

Chicago

Located on the shores of Lake Michigan, Chicago offers endless attractions for an unforgettable city break. Head to Navy Pier for amusements, fireworks, and entertainment, or explore River North for fresh air, quaint galleries, and unique gift shops. For stunning panoramas, visit the 103rd-floor Skydeck at Willis Tower, while foodies can indulge in Chicago’s famous deep-dish pizza at Gino’s East. Shopping on the Magnificent Mile and nightlife in Rush & Division promise excitement at every turn.

To enhance your trip, why not combine your time in Chicago with a self-drive adventure around the Great Lakes? Discover the natural beauty of Lake Michigan’s shoreline, the rugged splendour of Lake Superior, and the charming towns that dot this stunning region. It’s the perfect way to pair the vibrant energy of the Windy City with the breathtaking landscapes of the Midwest.

 

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

Where to Book

  • 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.

Rainfall

When to Visit

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

January

January in Chicago is marked by icy winds sweeping through the city, earning it the nickname "Windy City." While temperatures drop below freezing, indoor attractions like the Art Institute of Chicago and jazz clubs keep spirits warm.

February

As February continues the winter chill, the city's restaurants and theatres shine. Chicago Theatre Week offers excellent deals on performances, and hearty local dishes like deep-dish pizza become a must-try comfort.

March

March sees the city awaken with the festive St. Patrick’s Day celebrations, including the iconic dyeing of the Chicago River a vibrant green. Temperatures remain brisk, but the sense of fun and community warms the streets.

April

With April comes the promise of spring, as magnolias and tulips bloom in Millennium Park. The weather starts to warm, making outdoor walks along the Riverwalk more inviting, though layers are still advisable.

May

May offers pleasant temperatures around 18°C, drawing locals and visitors alike to the lakefront. Events like the Lincoln Park Wine Fest and farmers’ markets bring life to the neighbourhoods, while the gardens of the Chicago Botanic Garden are a delight.

June

June heralds the start of summer with highs reaching 25°C. Music fills the air with festivals like the Chicago Blues Festival, and rooftop bars buzz with activity. A visit to Navy Pier offers waterfront views and lively entertainment.

July

July in Chicago is vibrant, with sunny days perfect for boat tours on Lake Michigan. Temperatures hover around 28°C, ideal for exploring outdoor attractions like Grant Park and attending events like Taste of Chicago.

August

By August, summer is in full swing, and the city hums with activity. Beaches along Lake Michigan draw crowds, and the Chicago Air and Water Show adds excitement to the skies. The warmth lingers, but breezes from the lake offer respite.

September

September brings a gentle transition into autumn. Temperatures around 22°C make it ideal for strolling the Chicago Riverwalk or attending cultural festivals like the World Music Festival. The city feels alive but less frenetic than in midsummer.

October

October transforms Chicago with brilliant fall foliage in parks like Lincoln Park and Jackson Park. Crisp air sets the stage for seasonal activities, and Halloween celebrations bring fun and frights for all ages.

November

In November, the city embraces the holiday spirit with the opening of Christkindlmarket, a festive European-style market. As temperatures dip, warm mulled wine and twinkling lights make for a magical experience.

December

December wraps the year with festive grandeur, as the Magnificent Mile sparkles with holiday lights. Ice skating at Millennium Park and seasonal performances at local theatres make it a charming time to visit despite the winter chill.

Our Ratings

  • Most Recommended
  • Recommended
  • Highly Recommended
  • Not Recommended

Where to book


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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!

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