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Welcome to our ultimate guide to Chicago! The Windy City is a vibrant and dynamic destination with a rich history, world-class culture, and endless possibilities for exploration. Whether you’re a first-time visitor or a seasoned traveler, this guide has something for everyone.

From the iconic skyline and famous landmarks to the hidden gems and local secrets, we’ve compiled all the information you need to plan the perfect trip to Chicago. Learn about the best times to visit, top tourist attractions, and insider tips for a unique Chicago experience. We’ll also cover how to save money with the Chicago CityPASS, avoid crowds with crowd predictions, and plan your trip with travel guides. Plus, we’ll provide options for guided tours and excursions to help you make the most of your visit.

So let’s get started! Follow along as we explore the best of Chicago, from the bustling downtown to the charming neighborhoods and everything in between.

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Best Times to Visit

Chicago is a year-round destination with something to offer in every season. However, the best time to visit largely depends on your personal preferences and travel goals. If you’re looking to enjoy warm weather and outdoor activities, summer is the peak season with average highs in the 80s. However, this also means that hotels and flights will be more expensive, and crowds will be heavier.

Spring and fall are also great times to visit with more moderate temperatures and fewer crowds. Both seasons offer a variety of festivals and events, such as the Chicago Flower and Garden Show in spring and the Chicago Marathon in fall.

Winter in Chicago can be cold and snowy, but it also offers some of the best deals on hotels and flights, as well as holiday lights and events. If you don’t mind bundling up, you can enjoy ice skating at Millennium Park, shopping at holiday markets, and visiting the city’s many museums and indoor attractions. To get a more detailed breakdown of the best times to visit Chicago, be sure to check out our full post on the subject. Chicago’s weather can be extreme, with hot summers and cold winters. For a detailed breakdown of the weather in Chicago, you can check out this site:
SeasonAverage HighAverage LowNotable Events
Spring60-70°F40-50°FChicago Flower and Garden Show, St. Patrick’s Day Parade and Festival
Summer80-90°F60-70°FTaste of Chicago, Chicago Air and Water Show
Fall60-70°F40-50°FChicago Marathon, Chicago Food and Drink Festival
Winter30-40°F20-30°FChicago Christmas Tree Lighting, Winter WonderFest

Top Tourist Attractions

Chicago is home to a variety of top tourist attractions that are sure to keep you entertained during your visit. Some of the city’s most popular attractions include the Willis Tower, the Art Institute of Chicago, and Navy Pier. For a comprehensive guide to all of the best tourist attractions in Chicago, be sure to check out our full post on the subject.

Willis Tower: This iconic Chicago skyscraper was once the tallest building in the world, and it still offers some of the best views of the city from its Skydeck observation deck.

Chicago's Best Tours and Activities

Our choice of best things to do.

Art Institute of Chicago: Home to an impressive collection of art from around the world, the Art Institute is a must-see destination for art lovers.

Navy Pier: This popular waterfront destination is home to a Ferris wheel, an IMAX theater, and a variety of restaurants and shops.

For more information on these top tourist attractions and others, be sure to check out our full post on the subject.

Insider Tips for a Unique Chicago Experience

While Chicago is known for its world-class tourist attractions and events, there are also plenty of lesser-known experiences that can make your trip to the Windy City truly unique. Here are some insider tips for a one-of-a-kind experience in Chicago:

Gangsters and Ghosts Tour Chicago
  • Eat at a classic Chicago diner: For a taste of classic Chicago cuisine, be sure to check out one of the city’s many classic diners. Some popular options include the Original Pancake House, Lou Mitchell’s, and the Eggshell Cafe.

  • Take a stroll through one of Chicago’s many green spaces: From the formal gardens at the Garfield Park Conservatory to the sprawling lawns of Grant Park, Chicago has no shortage of beautiful green spaces to explore.

  • Visit a neighborhood festival: Each summer, Chicago’s neighborhoods come alive with a variety of festivals featuring live music, food, and other entertainment. Some popular options include the Taste of Chicago, the Chicago Blues Festival, and the Chicago Latino Film Festival.

  • Take a boat tour of the city: For a unique perspective on Chicago, consider taking a boat tour of the city. Options range from architectural cruises to sunset cruises on Lake Michigan.

  • Check out a comedy club: Chicago is known for its comedy scene, and there are a variety of comedy clubs scattered throughout the city. Some popular options include the Second City, the ComedySportz Theater, and Zanies Comedy Club.

  • Explore the city’s street art: From colorful murals to intricate graffiti, Chicago is home to a variety of street art worth checking out. Some popular areas to explore include Pilsen, West Town, and Wicker Park.

  • Go shopping at one of the city’s many markets: From the sprawling indoor market at the Randolph Street Market to the outdoor Green City Market, Chicago has no shortage of markets to explore.

  • Get a bird’s-eye view of the city: For a unique perspective on Chicago, consider taking a trip to the top of one of the city’s many skyscrapers. Options include the Willis Tower and the 360 CHICAGO observation deck.

Save Money with the Chicago CityPASS & other tips.

For travelers looking to save money on their trip to Chicago, the CityPASS is an excellent option. This discounted ticket package includes prepaid admission to five of the city’s top attractions: the Shedd Aquarium, the Field Museum, Skydeck Chicago, the Art Institute of Chicago (or the Museum of Science and Industry, 360 CHICAGO Observation Deck, or Adler Planetarium), and your choice of either the Art Institute of Chicago or the Museum of Science and Industry. By purchasing the CityPASS, travelers can save up to 48% on the cost of the same tickets purchased separately.

Some other ways to save money on your trip to Chicago include:

Best Value: Chicago CityPASS

We have done the math on the Chicago CityPASS. Read why we think it is worth buying.
  • Purchase tickets in advance: Many attractions offer discounts for tickets purchased online in advance.

  • Take advantage of free days: Many museums and cultural institutions offer free admission on certain days of the week or month.

  • Use your library card: Many libraries in the Chicago area offer free passes to local attractions through the Museum Adventure Pass program.

  • Eat like a local: Avoid touristy restaurants and opt for locally-owned and operated establishments for a more authentic and affordable dining experience.

  • Use public transportation: The Chicago Transit Authority (CTA) offers a number of passes and fares that can save you money on getting around the city.

By following these tips and considering the CityPASS, travelers can save money and make the most of their trip to Chicago.

Avoid Crowds with Crowd Predictions, Tips & Tricks

In this section, we will provide you with insights and tips on how to avoid crowds while exploring Chicago. Crowds can be a major deterrent for many travelers, as they can take away from the overall enjoyment of a trip. Fortunately, there are a few ways you can minimize your chances of running into large crowds while in the Windy City.

One of the most effective ways to avoid crowds in Chicago is to plan your trip during the city’s off-peak season. As mentioned earlier, spring and fall are typically the best times to visit Chicago, as the weather is mild and there are fewer tourists.

Another tip is to visit popular attractions during non-peak hours. For example, rather than visiting the Art Institute of Chicago on a Saturday afternoon, try going on a weekday morning or evening. The same goes for popular restaurants and other attractions.

Our daily crowd predictions

Check our daily crowd predictions for Chicago. We use lots of data to predict how busy it gets.

It’s also a good idea to stay informed about large events or festivals that may be taking place during your visit. These events can bring in large crowds and make it more difficult to navigate the city.

In addition to these tips, it’s also helpful to use crowd prediction tools and resources. There are several websites and apps that provide real-time crowd data for popular attractions in Chicago. By using these resources, you can plan your itinerary around the times and places that are likely to be less crowded.

Overall, with a little bit of planning and some insider tips, you can have a unique and enjoyable experience in Chicago without having to deal with large crowds.

Plan Your Trip with Travel Guides

Are you planning a trip to Chicago and looking for the best travel guide to help you make the most of your visit? Look no further! We’ve compiled a list of our top picks for travel guides to the Windy City.

Fodor’s Chicago: This comprehensive guidebook offers detailed information on everything from top tourist attractions to off-the-beaten-path neighborhoods and local festivals. With insider tips and recommendations from local experts, Fodor’s Chicago is a must-have for any traveler.

Chicago Like a Local: This insider’s guide is written by a team of local writers who know the city like the back of their hand. From trendy bars and restaurants to hidden gems and local events, Chicago Like a Local has everything you need to experience the real Chicago.

Walking Chicago: 35 Tours of the Windy City’s Dynamic Neighborhoods and Famous Lakeshore: As the title suggests, this guidebook is perfect for travelers who want to explore Chicago on foot. With 35 self-guided tours covering everything from the Loop to the North Side, Walking Chicago is a great way to discover the city’s diverse neighborhoods and cultural attractions.

No matter which guide you choose, you’ll be well-equipped to experience the best of Chicago. So start planning your trip today and make the most of your time in the Windy City!

Guided Tours and Excursions in Chicago

When it comes to exploring Chicago, guided tours and excursions can be a great way to see all that the city has to offer. From boat tours along the Chicago River to food tours through the city’s vibrant neighborhoods, there’s something for everyone.

Here are a few of our top picks for guided tours and excursions in Chicago:

  • Chicago Architecture Foundation River Cruise: This tour takes you along the Chicago River, showcasing over 50 of the city’s most iconic buildings and landmarks.
  • Chicago Food Planet Food Tours: Experience the tastes and flavors of Chicago on one of these food tours, which take you through neighborhoods like Chinatown, Wicker Park, and Little Italy.

Full overview of Chicago's Best Tours & Excursions

Read our extensive guide to Chicago's Best Tours and Activities
Top Picks
  • Chicago Trolley & Double Decker Co.: Hop on one of these trolleys or double decker buses to see all of the city’s top attractions, with the option to hop off and explore at your own pace.
  • Segway Experience of Chicago: See the city on two wheels with this Segway tour, which takes you through iconic neighborhoods like the Gold Coast and Old Town.

For a more extensive list of guided tours and excursions in Chicago, be sure to check out our post on the subject.

Conclusion: Start Planning Your Trip to the Windy City

To conclude, our ultimate guide to Chicago has provided you with valuable information on the best times to visit, top tourist attractions, insider tips for a unique experience, ways to save money with the Chicago CityPASS, and how to avoid crowds with crowd predictions and tips. If you’re looking to make the most of your trip to Chicago, consider taking a guided tour or excursion. From food and drink tours to architecture and history tours, there’s something for everyone. For more in-depth information on the best travel guides and books for your trip to Chicago, check out our post here. If you’re interested in exploring the city’s vibrant food and drink scene, be sure to check out Time Out’s recommendations for the best food tours in Chicago.

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