A rich history, vibrant waterfront and first-class food scene makes Chicago, IL, a favorite destination for museum buffs, sports fans, foodies and everyone in between. With its dizzying amount of cultural offerings, planning a weekend in the Windy City can feel like an impossible task. Fortunately our traveler community has already done the hard work for you. Here are their top tips on where to eat, play, and stay if you have just a few nights to enjoy the “City by the Lake”.


Opened in 1928, The Whitehall Hotel is located a short walk from some of Chicago’s top sites. “The location is perfect if you’re planning on exploring Michigan Avenue,” wrote one traveler. A recent multimillion-dollar renovation only adds to this boutique hotel’s charm. Added bonus: dogs are welcome!

Another popular destination for visitors is The Guesthouse Hotel, which offers multi-bedroom apartment suites and a home away from home type of experience. “Can’t say enough good things about the hotel, staff and our experience,” said one traveler, who described the suites as having fully stocked kitchens, full size fridges and ample appliances for cooking home-style meals (or at least reheating delicious leftovers from Chicago’s restaurants!)

Finally, The Langham, Chicago offers great views of the city, the Chicago River, and Lake Michigan. The Langham has been listed as one of the best hotels in the United States, if not the world. “Impeccable service, comfortable luxury, amenities galore!” wrote one traveler who has stayed at five-star hotels around the globe.

No matter which Chicago hotel you choose, you’ll find the lowest prices on TripAdvisor. We shop up to 200 sites to find you the best deal.


Chicago is the city that perfected the hot dog and gave us deep-dish pizza and Italian beef sandwiches. Whether you’re looking for iconic Windy City dishes or avant garde takes on international cuisine, Chicago more than delivers. Our travelers say eating out in Chicago is just as important as seeing the city’s sights.

The Publican serves family style dishes at communal tables, allowing you to enjoy good food and good company. The menu here changes daily and reflects the best seasonal and local ingredients available. “Take advantage of the chef’s tasting menu,” said one traveler, who described a lavish meal of oysters, pork belly, and decadent desserts. “Each dish had its own unique delicious flavor, there wasn’t a bad item sent to our table.”

Another popular destination for foodies is Avec. Applying a Midwestern sensibility to Mediterranean cuisine, Avec uses local ingredients to produce exotic combinations like sea urchin bruschetta, confit chicken paella, and pizza topped with butternut squash and jalapenos. Travelers say the hearty wine selection, with bottles ranging from $20 to $90, only adds to the restaurant’s appeal.

Named after a historic Chicago district dating back to the 1800s, The Gage features an inventive menu, impressive beer list, and convenient location just steps from The Art Institute of Chicago and Millennium Park. The menu boasts unique dishes like venison burgers, rack of elk, and a savory house poutine. “They had me at fried pickles,” wrote one traveler.

Of course no visit to Chicago is complete without a stop at Portillo’s for hot dogs or Al’s #1 Italian Beef for their famous beef sandwiches.


To see a lot in a short time, consider taking a tour of the Windy City sights that interest you most.

Departing from Riverside Gardens, Chicago’s First Lady Cruises takes you past some of the city’s most interesting architectural sites. Even if you’re not a building buff, our travelers say the open-air cruise is a must-do for visitors and residents alike. “This is a nice way to get an overview of the Loop area of Chicago,” said one traveler. “We actually like to take friends that visit us first on this tour because it’s relaxing and they get the general sense of the city before we hit individual points of interest.”

After getting your lay of the land, head up. Way up. The Skydeck Chicago sits on the 103rd floor of the Willis Tower, the tallest building in the Western Hemisphere. From here you can get a 360-degree view of the Windy City. A glass ledge juts from the observatory, allowing you to look down and see the street more than 1,300 feet below. Afraid of heights? Don’t worry. You can still get great views of the city without going on the glass ledge, said one traveler, who called the Skydeck a “must-do when in the city of Chicago!”

Another popular Chicago sight is the Lincoln Park Zoo. This free attraction is a favorite with kids and adults. The 35-acre zoo is home to more than 200 species of animals, including gorillas, monkeys, wolves and seals, as well as several rides for kids. “I would definitely recommend this zoo to family and friends,” said one traveler, “there is so much to see and do.”

To cover the rest of Chicago’s top sites, including Grant Park, Adler Planetarium, and Wrigley Field, take the Chicago Grand Half-Day Tour, which takes you through the best of the city’s famed north and south sides. “WOW”, said one reviewer, “What a great way to see the city.”