[Skip to Content]

Plan Your Next Staycation in the Loop

Loading

Posted  5 months ago  in  HotelsRestaurants and DiningLoop List

You’ve been working hard, and you need a vacation. But maybe taking a bunch of time off and dropping hundreds of dollars on a flight isn’t in the cards. The good news is you live in Chicago – why not make your next vacation a staycation right here in the Loop?


The Loop has everything you could want in a getaway: luxurious hotels, attractions known the world over, delicious food, and great options for shopping. With this guide, you’ll have your next vacation planned in no time. You may not be traveling far, but you’ll feel a world away when you put on your tourist hat.

Where to Stay

Luxury Hotels – The Blackstone Hotel

The Blackstone Hotel is a storied architectural icon rooted in the city’s legendary past but newly updated to deliver a distinguished hospitality experience for today’s discerning traveler. Previously known as the Renaissance Blackstone, this recently revitalized destination is blooming as a point of cultural and creative discovery on the Cultural Mile. This hotel offers modern accommodations with views of Lake Michigan and Grant Park, acclaimed dining at Mercat a la Planxa, craft cocktails and entertainment at Timothy's Hutch, refined meeting spaces, and thoughtful details like complimentary turndown service, 1600 CLUB Lounge, and more.

Learn More

Historic Hotels – The Palmer House

The Palmer House Hilton Chicago has been hosting visitors to the Chicago Loop for more than 140 years. This AAA four-diamond rated hotel continues to thrive in the heart of the theatre and financial district, steps from the Art Institute, Millennium Park, State Street shopping, and Grant Park, where summer festivals take place.

Learn More

Theatre District Hotels – Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown is a hotel for the curious, the adventurous, for those who see every journey as a chance to be inspired by the unexpected. Located steps from the Theatre District, this award-winning hotel blends recently renovated accommodations with thoughtful amenities and world-class service. After exploring the Theatre District, mingle at the hip rooftop bar while enjoying great views, delectable American cuisine, and terrific cocktails.

Learn More

Boutique Hotels – theWit Hotel

Boldly living in the heart of Chicago’s theater, arts, and shopping district, theWit Hotel stands as an homage to creativity and expression. With features like eye-popping design, stunning views, and innovative culinary creations, a stay at theWit is to experience an adventure that doesn't start until after you reach your destination. theWit houses two celebrated restaurants: State and Lake Chicago Tavern, which features regionally America fare and 16 artisanal beers on tap, and ROOF, the globally recognized lounge on the 27th floor that provides stunning views, small plates, cocktails, and world-class DJ entertainment.

Learn More

Pet-Friendly Hotels – Virgin Hotels Chicago

Does your furry friend need a break, too? Look no further than Virgin Hotels Chicago. It’s the first of its kind and the last hotel you’ll ever need, with the best food, work, and play all at your fingertips. Heartfelt delights meet seductive style at the charismatic Virgin Hotels Chicago. Step inside and find your new favorite space, where the doors are never closed, and the minds are always open.

Learn More

Budget-Friendly Hotels – Cambria Chicago Loop – Theatre District

The Cambria Chicago Loop - Theatre District is an uncomplicated, service-minded option for leisure travelers like yourself. Located in the heart of Chicago's Loop, and half a block from State Street Shopping District, the Cambria Chicago Loop boasts 199 sleeping rooms and 2,100 square feet of space for adaptable meetings and events, along with a full-service restaurant and bar open daily for breakfast and dinner. The Cambria Chicago Loop - Theatre District, located in the same building as the Oriental Theatre, provides guests with an upscale but never uptight feel with each visit.

Learn More

Hotel Spas – Hilton Chicago

Hilton Chicago features more than 1,500 guest rooms, more than 234,000 square feet of flexible function space, modern amenities, and more – and the spa is to die for. In fact, Hilton Chicago has something for all your wellness needs. With a well-equipped, modern facility, you can find Chicago's only indoor jogging track, in addition to whirlpool, a heated indoor pool, and massage services. Sounds relaxing, doesn’t it?

Learn More

Hotel Rooftops – Cindy’s at the Chicago Athletic Association Hotel

The jewel in the crown of Chicago Athletic Association Hotel, Cindy's is a rooftop restaurant and open-air terrace overlooking Millennium Park and beyond. Atop the Chicago Athletic Association Hotel, Cindy's boasts magnificent views of Millennium Park, the Art Institute of Chicago, and Lake Michigan. The award-winning menu created by Executive Chef Christian Ragano features family style classic comfort food, bio-dynamic wines, and award-winning cocktails with large format apothecaries. Reservations are available for lunch, dinner, cocktails, and weekend brunch.

Learn More

What to Do

The Art Institute of Chicago

The Art Institute is the second largest art museum in the country with a collection of approximately 300,000 works of art. The museum collects, preserves, and interprets works of art of the highest quality, representing the world's diverse artistic traditions, for the inspiration and education of the public and in accordance with the profession's highest ethical standards and practices. With an annual visitation of about 1.5 million, the Art Institute is one of the most popular attractions for Chicago residents and visitors alike.

Learn More

The International Museum of Surgical Science

The International Museum of Surgical Science offers over 10,000 square feet of public galleries committed to the history of surgery and an exquisite permanent collection of art and artifacts from the history of medicine. One of the museum’s most fascinating pieces is an iron lung, which polio sufferers would lie inside in order to breathe. See an iron lung and learn more about medical history at what the Washington Post called “Chicago’s creepy cabinet of curiosities.”

Learn More

Click here to explore more galleries and museums.

The Goodman Theatre’s ‘Twilight Bowl’

Check out Rebecca Gilman’s play Twilight Bowl starring an all-female cast at Goodman Theatre. Six young women. One small town. Different lanes. After graduating from a small Wisconsin high school, Sam heads to college on scholarship—but her cousin Jaycee’s future isn’t looking as bright. As the young women and their friends face adulthood, their local bowling alley becomes a place to celebrate triumphs, confront challenges, and forge new identities. With her signature grace, wit, and compassion, Rebecca Gilman (Luna Gale, Boy Gets Girl) questions the blueprint for a successful life and embraces the unknown on the road ahead. Playing now through March 10.

Learn More

Chicago Architecture Center

The Chicago Architecture Center (CAC) is a non-profit organization dedicated to inspiring people to discover why design matters. The CAC offers tours, exhibitions, programs and events for all ages. Last year, the Center opened in a new location at 111 E. Wacker Drive, occupying 20,000 square feet with interactive exhibitions, a lecture hall, a hands-on design studio, retail space, and offices. But if it’s a tour you’re after, you’ve got options. The Center leads boat tours, bus tours, bike tours, walking tours, L train tours, and private tours—in the Loop and beyond. Everything you ever wanted to know about Chicago architecture, you can learn from the CAC.

Learn More

Click here to explore more tours.

Maggie Daley Park

Maggie Daley Park, a 22-acre public park open year-round and located on Chicago's lakefront, is a welcoming, urban retreat for children and adults of all ages. The free and interactive park offers children's play areas, rock climbing, a Skating Ribbon, tennis courts, and a fieldhouse, as well as picnic groves and a beautiful Cancer Survivors' Garden.

Learn More

American Writers Museum

The American Writers Museum is the first museum in the nation devoted to American writers and their works. Through innovative and dynamic state-of-the-art exhibitions, as well as compelling programming, the American Writers Museum educates, enriches, provokes, and inspires visitors of all ages. Some of the museum’s interactive exhibits include a “Word Waterfall” that combines the dynamic animation of words from featured works with imagery and soundscape, the “Surprise Bookshelfs” that include edge-lit boxes each with a hint on its face about an example of American writing, and “The Mind of a Writer Gallery” with its giant rolls of paper suspended from the ceiling to an easel, providing the o

Learn More

Click here to explore more family-friendly activities.

Where to Eat

Brunch – AceBounce

AceBounce offers an all-inclusive social experience, combining three elements of hospitality: bar, restaurant, and high energy entertainment—Ping Pong. The quality food and drink menu is attentively curated by a local team, including James Beard award-winning chef and accomplished mixologist, Rick Gresh. AceBounce's menu exhibits a mixture of American, Mediterranean, and Asian influences, concentrating on high-quality ingredients and featuring local farmers and artisan producers.

Learn More

Lunch – Latinicity Food Hall

Chef Richard Sandoval combines the warmth of Latin American dining with an authentic and vibrant street food environment at Latinicity Food Hall and Lounge on the third floor of Block 37. Here, you can keep it casual without sacrificing quality, and you can take advantage of a variety of options. Especially if you’re eating with a group, there’s no better lunch spot for you.

Learn More

Dinner – Italian Village Restaurants

As the oldest and most celebrated Italian restaurant, Italian Village Restaurant has the largest wine cellar in the entire Midwest with over 45,000 bottles. With three restaurants in one historic building, it is home to The Village, La Cantina Chophouse, and Vivere, boasting 87 years of traditional Italian dishes.

Learn More

Happy Hour – The Berghoff

Proudly serving German cuisine with an American twist for more than 114 years, The Berghoff Restaurant is a Chicago classic. It features a full-service dining area, bar, and lower level casual dining area called the Berghoff Café. This restaurant is known for family tradition and proudly displaying the city's first-ever liquor license. There’s never been a better time to pay The Berghoff a visit, as it just opened Adams Street Brewery. That’s just about the best Happy Hour combination you could ask for.

Learn More

Click here to explore more dining options.

Where to Shop

Clothing & Accessories – Macy’s

Macy's has the latest in women's and men's clothing, accessories, jewelry, beauty, shoes, and more. Visit this Macy's flagship destination and experience history come to life every day. Macy's on State Street is the second largest department store in the world, is recognized as a National Historic Landmark, and is listed on the National Register of Historic Places. Customers can shop and dine their way through the building that has been a tradition for generations of Chicagoans.

Learn More

Health & Beauty – Merz Downtown

Located at the main entrance of the historic Palmer House Hotel, Merz Downtown offers an unsurpassed selection of natural health, beauty, and personal care, men's grooming goods, fine skin care, and niche fragrance from around the world. With more than 15,000 products, a knowledgeable staff, and a relaxed, friendly atmosphere, Merz Downtown is a veritable Chicago landmark and must-shop destination for locals and travelers alike.

Learn More

A Little of Everything – Block 37

Block 37 is a hip and urban shopping, dining, and entertainment destination spread out over an entire block in the heart of Chicago’s Loop. Structured around a five-story atrium, Block 37 is home to an ample selection of the best fashion and beauty brands, while also hosting a list of cafés, boutiques, and other essential conveniences. Learn More

Click here for a listing of other places to shop.