As the saying goes, there's never a dull moment in the Windy City. From its world-renowned architecture and museums to its vibrant neighbourhoods and Lake Michigan waterfront, Chicago has something to offer everyone - read our guide to Chicago.
Whether you're a first-time visitor or a longtime resident, we've put together a comprehensive guide to everything Chicago has to offer. From where to stay and what to eat to what to see and do, this guide has everything you need to plan your perfect trip.
So, what are you waiting for? Start planning your trip to Chicago today!
SPONSORED: Links in this color go to our partners.
Getting to Chicago
Have you always dreamed of visiting the Windy City? Chicago is one of the most iconic and vibrant cities in the United States, and there's so much to see and do!
If you're looking for an unforgettable city break, then look no further. Chicago is a major transportation hub, with flights arriving into both O'Hare (ORD) and Midway airports. O'Hare has direct flights to all parts of the world! You can also get to Chicago by train or bus from a number of nearby cities.
Once you're in Chicago, getting around is easy. The city is well-served by a comprehensive public transport system, or you can explore on foot or by bike.
Accommodations in Chicago
In order to make the most of your time in Chicago, it is important to find accommodation that is convenient and within close proximity to all the sights and sounds the city has to offer.
There are a plethora of accommodation options in Chicago, ranging from budget-friendly hostels to luxurious five-star hotels. However, one of the best options for tourists is to stay in a hotel located in the heart of downtown. This way, you can easily walk to all the major tourist attractions and not have to worry about wasting time on public transportation.
Some of the best hotels in downtown Chicago include The Peninsula Chicago, The Ritz-Carlton, and The Langham Chicago. So whatever your budget or preferences may be, there is sure to be an accommodation option that suits your needs!
Hotel options - luxury
- Luxury: The Peninsula Chicago is located in the heart of downtown Chicago. The hotel features a distinctive Art Deco design and is close to famous attractions like The Magnificent Mile, Willis Tower, Navy Pier and Lincoln Park.
- Luxury: The Ritz-Carlton, Chicago - This luxurious hotel features elegant rooms with marble bathrooms and city views. Guests can enjoy fine dining at Torali Italian-Steak, the hotel's on-site restaurant, as well as a fitness center and indoor pool.
- Luxury: Four Seasons Hotel Chicago - This 5-star hotel offers luxurious rooms with city views and marble bathrooms. Guests can enjoy a fitness center, an indoor pool, and a spa. The hotel also has an on-site restaurant and bar.
- Luxury: The Langham Chicago is a luxury hotel located in the River North neighborhood of Chicago. The hotel also has a number of dining options, including the award-winning Travelle Kitchen + Bar, which serves contemporary American cuisine, and the Pavilion, a rooftop lounge and terrace with stunning views of the city.
Mid-Range options
- Mid-Range: The Drake Hotel - This historic hotel offers elegant rooms with city views and marble bathrooms. Guests can enjoy a fitness center, an indoor pool, and a spa. The hotel also has on-site dining options, including the Coq d'Or bar and the Palm Court restaurant.
- Mid-Range: The Talbott Hotel - This 4-star hotel offers spacious rooms with city views. Guests can enjoy a fitness center and an on-site restaurant. The hotel is also conveniently located near many of Chicago's top attractions.
- Mid-Range: Kimpton Hotel Monaco Chicago - This 4-star hotel offers stylish rooms with city views. Guests can enjoy a fitness center, an indoor pool, and a sauna. The hotel also has an on-site restaurant and bar.
Economy hotels
- Economy: The Willows Hotel - This 3-star hotel offers comfortable rooms with city views. Guests can enjoy a fitness center and an on-site restaurant. The hotel is also conveniently located near many of Chicago's top attractions.
- Economy: Aloft Chicago Mag Mile s a modern, budget-friendly hotel located in the heart of downtown Chicago, Illinois. It's located in the iconic Magnificent Mile, which is known for its high-end shopping, dining, and entertainment options.
- Economy: The Travelodge Chicago - This budget-friendly hotel offers simple rooms with city views. Guests can enjoy a fitness center, and the hotel is conveniently located near many of Chicago's top attractions.
Restaurants and Drinking Spots in Chicago
Now that you've got an idea of all the amazing things to see and do in Chicago, it's time to eat! Chicago is a foodie's paradise, with options to satisfy every craving.
There are endless restaurants to explore in the city, but we'll give you a taste of some of our favourites. For Italian food lovers, we recommend checking out RPM Italian or DineAmic Group. If you're in the mood for some delicious barbecue, Smoke Daddy is definitely worth a visit. And for those who love seafood, try Shaw's Crab House or Catch 35.
Of course, Chicago is also home to some incredible breweries, bars, and pubs. Some of our favourites include Revolution Brewing, the Green Mill Jazz Club, and The Publican.
Exploring the City: Attractions and Things to Do
Now, letโs get to the fun part: exploring the city! Chicago has so much to offer visitors, from attractions and activities to some of the best food and drink around. Whether youโre looking for a leisurely stroll through some of the cityโs wildest parks or an adventurous bike ride down its stunning lakefront paths, Chicago has something to keep everyone entertained.
The Magnificent Mile along Michigan Avenue is a must-see for any out-of-towner; here you can find iconic historic landmarks, top-notch shopping, vibrant nightlife and spectacular views of downtown. Stroll through Navy Pier and enjoy their many events, restaurants and shops or go old school at Wrigley Field and see the Cubs play at this iconic stadium. And when youโve worked up an appetite, dig into some authentic deep-dish pizza or sample Chicago-style hot dogs from one of the cityโs famous eateries.
360 Chicago Observation Deck offers breathtaking panoramic views of Chicago from 1,000 feet above the famed Magnificent Mile, or the Chicago Skydeck. Step outside the third tallest building in the Western Hemisphere. At 1,353 feet in the air, the Ledgeโs glass boxes extend out 4.3 feet from the Skydeck.
Chicago is a city like no otherโvisit it today!
Leisure Activities in Chicago
If youโre looking to relax and have a good time, Chicago has plenty of options for you. From taking a leisurely stroll along the city's iconic lakefront to exploring one of the largest public parks in the world, there are endless ways to spend your day in this vibrant destination.
You can enjoy a relaxing boat ride down the Chicago River, watch a game at Wrigley Field (the legendary home of the Chicago Cubs), or take a tour of some of the most interesting architectural landmarks in the world. If you fancy ice hockey or basketball, United Center is your place! The home of Chicago Blackhawks and Chicago Bulls. There are also plenty of outdoor cafes and restaurants near popular attractions; perfect for grabbing a bite to eat with family and friends. With its rich history, cultural diversity, and abundance of activities to choose from, Chicago is an ideal vacation spot for leisure travellers.
Chicago's Culture and History
You can't talk about Chicago without talking about its unique culture and history. Rich with art, food, history, and entertainment, it's no wonder that Chicago is a popular destination for tourists. From the Art Institute of Chicago to the amazing architecture of the Wrigley building and Marina City Towers, the Windy City is sure to be a memorable experience.
When it comes to food, no matter what you chooseโdeep dish pizza, hot dogs or Italian beefโyou can be certain you're in for a delicious treat. Culture-wise, there's plenty to explore too: from sports teams like the White Sox and Bears to theatre productions at Steppenwolf Theatre Company and Goodman Theatre. And if you're looking for something more historically-minded, why not check out the city's various museums like The Field Museum of Natural History or The Museum of Science and Industry? No matter what interests you have, there's something for everyone in this great city!
The start of Route 66
Chicago is considered the starting point of Route 66, as it begins on Adams Street at Michigan Avenue. The "Mother Road" as it's often referred, is a historic highway that runs from Chicago to Santa Monica, California, and it's considered one of the most iconic roads in America.
Route 66 was first established in 1926 as one of the first highways in the United States. It was created to connect the major cities of the Midwest, including Chicago, to the West Coast.
For tourists visiting Chicago, taking a trip down Route 66 is a must-do experience. You can rent a car and drive the entire route, or take a shorter trip and visit some of the most famous landmarks and attractions along the way, such as the Route 66 Museum in Pontiac, Illinois, and the Route 66 Drive-In Theater in Springfield, Missouri.
In recent years Route 66 has become a popular tourist destination, many landmarks and businesses have been preserved and now advertise themselves as a part of the route. And many people still drive it as a way to connect with American history and culture.
Conclusion on this Chicago guide
You will not regret reading this guide! We highly recommend you start by booking your accommodation and restaurant reservations, as Chicago is definitely a city that deserves to be explored to the fullest!
Other city guides: