[Skip to Content]

A 24-hour itinerary for the Chicago Loop

Posted  3 years ago  in  Trending, Things to Do

5 MIN READ – There’s way too much to do and see in the Chicago Loop for just a quick trip. Check out this 24-hour itinerary to make the most of your time downtown.


Good Morning

Lakefront Trail

Go for a morning walk or bike ride and watch the sunrise on the Lakefront Trail. These trails run along Lake Michigan and give access to the lake for recreational activities. As you go along these trails, you can see a beautiful view of the skyline and the magnificent park space on the edge of the city.

Chicago Riverwalk

Read a book along the Chicago Riverwalk. Feel as if you're floating as you take in the view of the city along the water. This pathway rests along the bank of the Chicago River for an exclusive view of world-class architecture, with a variety of restaurants, bars, and attractions along the way. 

Breakfast

Goddess and the Baker is a casual, laid back, gourmet storefront that serves fast and fresh food, perfect for your morning coffee and breakfast. There are several locations in the Loop, including outdoor patios so you can soak up the morning sun. Or enjoy brunch at the Walnut Room, the first restaurant in a department store. The space is exquisite with beautiful Circassian walnut paneling and Austrian crystal chandeliers. This elegant and comfortable dining experience offers delicious meals, cocktails, and a variety of wines. Definitely try Mrs. Hering’s chicken pot pie, which has been a favorite on the menu since the 1880s. Make reservations for the Walnut Room here.

Afternoon

Shoreline Sightseeing

Shoreline’s Architecture River Tour makes a great centerpiece of a day or evening in the city when the sun is high in the sky and the buildings and water glisten in the light. Take in 40 of Chicago’s famous landmarks on this 75-minute Chicago River tour. Relax and enjoy the ride with close-up views and excellent photo opps. Fireworks Tours are on Wednesdays and Saturdays. Daily water taxis are available as well. Find out more here or call 312-222-9328.

Museums

Wander through the Art Institute of Chicago and see historical pieces as well as contemporary works in the Modern Wing. Come across avant garde photos at the Museum of Contemporary Photography. Swing by the Museum of Illusions and be amused by the world of illusions where you can truly experience the impossible. Check out more museum options in the Loop here.

Eat & Drink 

Go to City Winery for a classy outdoor patio experience along the Chicago River. Beatnik on the River is an exotic escape with food from around the world and eccentric cocktails. Their riverfront patio is decorated with Indonesian daybeds, Moroccan lanterns, and plush greenery. For fine German cuisine fused with classic American food, come to the Berghoff. With its rich history and delicious food, the Berghoff reopens on July 12 after hibernating due to COVID-19. Find more dining options here.

Shop

Shop on State Street and beyond with plenty of great retail options throughout the Loop. Pick up essentials at Target in its convenient downtown location. For a sophisticated, clean look, shop Zara. Get deals on designer clothing at Nordstrom Rack. Shop Sephora for cosmetics with over 300 brands to choose from. Walk through Block 37, an indoor retail, dining, and entertainment destination that covers an entire block in the Chicago Loop.

And you absolutely must shop at Macy’s on State Street for your fashion, beauty, and home needs. Take a break from the heat to explore the store’s seven floors. Along with an excellent shopping experience, appreciate the history of this national historic landmark. The Great Clocks adorn each corner of the building’s exterior, the Circassian walnut paneling and Austrian crystal chandeliers are exquisite features of the Walnut Room, and view the ornate Tiffany Ceiling that features 1.6 million pieces of iridescent glass. There is also a Visitor Information Center, where Go Chicago Explorer passes are available for purchase. Find out more here, and see more shopping options in the Loop here.

Nightlife

Rooftops

Take your night to a whole new level at one of the Loop’s finest rooftop bars, offering some of the best views in the city. Consider ROOF on theWit for a modern, Mediterranean ambience; Cindy’s for a stellar view of Millennium Park; LondonHouse Rooftop Lounge for the height of luxury; IO Godfrey Rooftop Lounge for hip, chic vibes; Raised for an incredible view of the Chicago River and skyline; or AIRE for cozy fire pits and 360-degree views.

Flight Club

Flight Club is a multi-award-winning venue that offers social darts experience. In addition to the fun and games in this venue, there is a great atmosphere, a bar serving specialty cocktails, and delicious food. For the ultimate night out, Flight club is right on target.

Acebounce

If you’re more of a ping-pong fan, check out AceBounce. The Parlor private room at AceBounce is comfortable and exclusive with blacklight ambiance and a cool atmosphere. There is a cocktail bar with a dedicated bartender, three beautiful turned wood models of the original Jaques ping pong tables, and a Games Guru Experience.  For the perfect night out, AceBounce is a hit.

Overnight

Find a room with exclusive access to Chicago culture, food, attractions, and shopping. Hotels offer a luxurious stay or an affordable one. A unique stay or a classic one. A lavish stay or a practical one. Choose the hotel that is right for you. The JW Marriott Chicago is a landmark hotel with a deep history. Visit their prime location in the Chicago Loop, just steps away from several great attractions. After a day on the go in the city, relax in the on-site spa, reserve a swim in an indoor lap pool, exercise in a modern fitness center, and eat at The Florentine. To view their offers, click here. Book JW Marriott Hotel here.

The Palmer House Hilton is one of Chicago's most luxurious and iconic hotels, featuring immaculate guest rooms, event, and meeting space, and it is ideally situated in the heart of downtown. Go shopping, relax at the spa, dine at the best restaurants in town, or stay in. Be sure to go for a swim, with the addition of a new indoor pool. Book the Palmer House here.

Hilton Chicago, a historic hotel that first opened its doors in 1927, is one of Chicago’s largest hotels. It’s the ideal stay for those looking for great lake and Grant Park views. Enjoy a state-of-the-art spa and fitness center, or entertain coworkers and friends in the phenomenally equipped meetings and events spaces. Book the Hilton Chicago here.

In the heart of Chicago’s theater, arts, and shopping district, theWit Hotel boldly stands as a tribute to creativity and expression. With a modern design and strong lines, the architecture of theWit offers stunning views. A newly renovated rooftop bar, ROOF on theWit, and ballroom event spaces serve to entertain you and host events. They also offer expressive culinary creations, engaging service, and advanced technology. TheWit is a Four Diamond, multi-sensory hotel, facilitating a memorable experience. Book theWit here.

See more hotel options here, and book an unforgettable end to your 24 hours in the Loop. You might find you want to stay a little longer.

Exclusive Loop deals, recommendations, and news direct from Chicago Loop Alliance.