40 Tips I Wish I Knew Before Visiting Chicago
Discover the best of Chicago with this curated guide to its iconic attractions and hidden gems. From the shores of Lake Michigan to vibrant neighborhoods, explore the Windy City's rich history, diverse culture, and culinary delights.
Navy Pier
A large, impressive pier, but potentially a tourist trap. Locals use it for strolling and enjoying the views.
Lakefront Trail
A gorgeous area to walk and take in the sights, popular with locals, especially in warmer months.
Chicago Riverwalk
A beautiful area to walk through with restaurants, cafes, and bars. Popular with locals and tourists alike.
Chinatown
Accessible via the water taxi, offering an affordable way to see the city from the water.
Chicago Athletic Association hotel
A hotel with a beautiful lobby, game room, and rooftop bar called Cindy's, offering charm and character.
Cindy's Rooftop Bar
A rooftop bar located in the Chicago Athletic Association hotel.
Cloud Gate
Also known as "The Bean", it's a popular spot for tourists to visit, but perhaps overrated as a focal point of a trip to Chicago.
Wrigleyville
An area to visit when the Cubs are playing at home to experience the culture of Chicago.
Wrigley Field
The home field of the Chicago Cubs, a great place to experience Chicago's sports culture.
Guilt Bar
A cozy, speakeasy-style bar with fantastic food and a great vibe. Reservations are recommended.
Portillo's Hot Dogs
A fast-food place downtown where you can try an Italian beef sandwich and a Chicago hot dog.
Sugar Moon Bakery
The best spot to get pastries, though it's in a more local area and requires higher effort to get to.
The Doughnut Vault
A spot in the center of the city with the best doughnuts, worth the effort if you arrive early enough.
Metric Coffee
A fantastic place to get a high-quality cup of coffee, requires more effort to get to.
Three Arts Club Cafe
A gorgeous spot for coffee in a beautiful building, near the tourist areas, although the products aren't the best.
Fulton Market
A cool, young area on the outskirts of the city, great for nightlife and restaurants. A good place to both stay and hang out.
Gold Coast
A gorgeous and safe area, a bit upscale and pricey, close to the beach, Magnificent Mile, and Lincoln Park. Good access to public transit.
Streeterville
Not recommended for visiting or staying, as it's too far from public transit and lacks unique attractions.
Lincoln Park
A gorgeous and very safe area on the north side, with a residential feel. Great to visit, but not ideal for staying as a first-timer.
River North
A popular place amongst tourists, good for both visiting and staying, with great food options but also tourist traps. Centrally located.
The Loop
Not recommended for staying or visiting, mostly a business district that clears out at night. Focus on the outskirts of the Loop.
Logan Square
A more residential area with a young atmosphere and affordable options. Great to visit for a local feel, especially during festivals, but not the best place to stay for a short trip.
Wicker Park
A more residential area with a young atmosphere and affordable options. Great to visit for a local feel, especially during festivals, but not the best place to stay for a short trip.
O'Hare International Airport
The bigger, international airport, about a 50-minute ride to the Loop.
Midway International Airport
More convenient and less packed than O'Hare if flying domestic and using public transit, about a 25-minute ride to the Loop.
Magnificent Mile
A magnificent shopping and tourist district, but tourists should not get trapped there and should explore other areas for better restaurants.