7 Days in Chicago Itinerary
Guides and Itineraries,  USA

7 Days in Chicago Itinerary: Discovering the City’s Hidden Gems

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Chicago is an energetic city with a rich history of commerce and industry. If you’re planning a trip to the Windy City and want to make the most of your time, a well-planned itinerary can help. In this article, we’ll share a 7-days itinerary in Chicago as suggested by a local, covering some of the top attractions in Chicago — from the iconic Willis Tower to the beautiful Millennium Park and Art Institute of Chicago. This one-week itinerary can help you navigate the city whether you’re a first-time visitor or returning one.

About Chicago

Founded in 1833, Chicago has become a significant business hub in the Midwest region of the United States with over 2.7 million residents. It is a popular destination for tourists and visitors, with its wealth of landmarks, museums, and entertainment venues.

If you have never visited Chicago, here are just a few reasons to add it to your bucket list of travels:

  • While there are numerous things to visit on land, the city is surrounded by one of the Great Lakes, where you may also participate in fun water activities.
  • Chicago is a fantastic culinary city with some of the top restaurants in America. The city has world-class museums displaying everything from art to natural history to architecture.
  • Millennium Park, which includes Cloud Gate (called “The Bean”), Buckingham Fountain, and The Crown Fountain, is one of the top free attractions. 
  • The Taste of Chicago, Chicago Jazz Festival, Chicago Summer Dance, and Chicago Blues Festival are all annual festivals where you can enjoy free entertainment. 

Tips for Staying in Chicago

Your budget will play a significant role in deciding which hotel to stay in during your stay. Generally speaking, the closer you are to the Loop and Magnificent Mile, the higher the hotel rates. However, if you plan ahead you can score some great deals. Here are some tips for staying in Chicago that are recommended by a local. 

  • Consider other neighborhoods, such as the far north, or even a suburb such as Oak Park, if your budget is limited. The location should also be easily accessible by train with a commute of no more than 30 minutes.
  • Keep in mind major city events like Lollapalooza and holiday weekends like July 4th and Memorial Day. During these times, hotel rates will be extremely high. 
  • Renting a car is not a good idea. Chicago parking is very expensive, with citations starting at $90. The cost of parking for a full day is about $25, while valet parking is even more expensive.  
  • There are various options for getting around town, including car sharing (Uber, Lyft, Taxi), Chicago Elevator Trains (or the ‘L’), and city buses. More essential, make sure you understand how to navigate Chicago securely. 
  • As with any city visit, keep vigilant and mindful of your surroundings. Never put yourself in danger when out exploring.
Cloud Gate in Chicago
Cloud Gate in Millennium Park.

7 Days in Chicago Itinerary

Chicago’s attractions are seemingly endless, catering to all types of travelers. You can enjoy water activities in the Great Lakes or explore its diverse culinary scene in the many award-winning restaurants. Chicago is also home to world-renowned museums like the Art Institute of Chicago that showcase everything from art to natural history to architecture. Some of the city’s best attractions, such as the Cloud Gate, Buckingham Fountain, and The Crown Fountain, can be visited for free in Millennium Park. 

We think a good itinerary should have a nice mix of things to do that will not break the bank or wear you out. It should also stimulate the mind, body, and spirit of travelers. With that said, here is a 7-day itinerary for visiting Chicago that is recommended by a local. It is designed for you to see the city at a less frenzied pace and allow you to swap the activities so that they fit your preferences and interests.  

Day 1

Morning: Start the day with a guided tour of the iconic Chicago architecture on the Chicago River Cruise. This is one of the most popular tours in Chicago and gives travelers a relaxing view of the city from a different perspective than a tour bus. 

Chicago river cruise
Chicago river cruise.

Afternoon: Head over to the Art Institute of Chicago to admire world-famous works of art. You’ll see works of Impressionism, and modern art, as well as incredible sculptures from around the globe. 

Exhibit at Art Institute of Chicago
Exhibit at Art Institute of Chicago.

Evening: Explore the historic Navy Pier, grab some dinner at one of the pier’s many restaurants, and take a ride on the Ferris wheel to see the city skyline. The pier is a great place to watch the boats float by or sit on the wave wall to relax. There is also free recreation in the summer ranging from bands to street entertainers. 

Day 2

Morning: Enjoy a traditional Chicago-style breakfast at Lou Mitchell’s, famous for its pancakes, waffles, and omelets. It is one of the oldest restaurants and a great stop if you love diner food. Another great option for a phenomenal breakfast is Wildberry Pancakes & Cafe on Michigan Ave, or Little Goat Diner in the Fulton Market neighborhood.

Afternoon: Take a food tour of Chicago’s diverse neighborhoods, tasting everything from deep-dish pizza to hot dogs and Italian beef.

Evening: Experience the Chicago brewery scene with a visit to Revolution Brewing Company or Half Acre Beer Company. Optionally, if you prefer a glass of wine with musical performances, visit City Winery. There are two locations, one is downtown on the Chicago Riverwalk, the other is in the West Loop.   

Day 3

Morning: Take a stroll on the Lakefront Trail along Lake Michigan. If you want to cover more sights in a short amount of time, there are bicycle rentals available at Navy Pier’s Bike and Roll, or you can find a station to use Chicago’s bike share program, Divvy. 

Afternoon: Visit one of Chicago’s beaches such as North Avenue Beach or Oak Street Beach and rent a paddleboard or kayak.

Oak Street Beach in Chicago
Oak Street Beach.

Evening: Watch the sunset over the lake while sipping a cocktail at a rooftop bar. Cindy’s Rooftop is located at 12 S. Michigan Ave and it’s near the Art Institute. If you visit the museum, dining at Cindy’s would be a nice option. Other nice rooftop bars in the downtown area include London House (85 E Wacker) and RAISED (1 W Wacker).

Day 4

Morning: Visit the Museum of Contemporary Art Chicago to see modern and contemporary art exhibits.

Afternoon: Check out the National Museum of Mexican Art to learn about Mexican culture and art. It is in the Pilsen neighborhood and can be easily accessed via the pink line of the Chicago ‘L’ train. The elevator train is the best way to get around Chicago. Take the pink line west and exit at the 18th Street stop. The museum is a 7-minute walk from the station.    

Evening: Attend a performance at the world-renowned Chicago Symphony Orchestra. A classical performance would be an enriching cultural immersion while visiting the Windy City.

Chicago Symphony Orchestra
Chicago Symphony Orchestra. (Photo by Todd Rosenberg)

Day 5

Morning: Start the day with a yoga class at one of Chicago’s many studios.

Afternoon: Pamper yourself with a spa treatment at the Peninsula Chicago or the Four Seasons. At these five-star hotels, you can indulge in luxurious amenities during your visit. Or visit the famed Kohler Waters Spa in Lincoln Park for a rejuvenating experience including massages, facials, and body treatments that are all designed to soothe and refresh both body and mind.

Evening: Enjoy a peaceful walk through the Lincoln Park Conservatory and Gardens. If you are traveling with kids or looking for nature and wildlife in the city, the Lincoln Park Zoo is one of many free amenities in Chicago. 

Lincoln Park Nature Boardwalk in Chicago
Lincoln Park Nature Boardwalk.

Day 6

Morning: Take a tour of the legendary Wrigley Field. Are you traveling with sports enthusiasts or want to see the legendary field of the Chicago Cubs, then add this tour to your travel plans. Wrigley Field can be reached by the Red Line of the Chicago ‘L’ train (exit at the Addison station). The neighborhood is also a great area to explore for nightlife.  

Afternoon: Shop till you drop on the Magnificent Mile, Chicago’s famous shopping district. You can visit high-end designer stores like Gucci, Louis Vuitton, and Bulgari then stop at the World’s Largest Starbucks for a cup of joe after a late lunch.

Evening: Visit 360 Chicago for unparalleled views. From the observation deck, you’ll see Chicago to the east and Lake Michigan to the west. The TILT is an optional experience that suspends you over the city from the 94th floor.

Day 7 

Morning: Visit the iconic Willis Tower and step out onto the Skydeck for stunning views of the city. Compared to 360 Chicago, this observatory is from a higher point as the deck is on the 103rd floor. You can also enter the glass-floor observation for fun photos.

Willis Tower in Chicago
Willis Tower.

Afternoon: Take a stroll along the riverwalk to see the city from a different angle. If you tasted Chicago’s deep-dish pizza, stop at Lou Malnati’s (439 N Wells) or Giordano’s (730 N Rush) for some delicious pie from a pan. 

Evening: Experience the vibrant nightlife scene in Chicago’s Wicker Park neighborhood, with its many bars and restaurants. Exploring one of the city’s neighborhoods is truly for those with a sense of adventure. You can get to the area by taking the blue line Chicago ‘L’ train and exiting the Damen stop. Stop at Ina Mae (1415 N Wood) for great southern cuisine with a New Orleans vibe, or The Violet Hour (1520 N Damen) for a sophisticated artisanal cocktail with a speakeasy atmosphere. 


In conclusion, Chicago is a city full of life and entertainment. With this itinerary with recommendations from a local, you can be sure to have a great experience that most visitors would not know about.  Explore the suggested range of attractions, neighborhoods, and transportation options, and experience the best of the city! 

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