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Plan Your Next Staycation in the Loop

Posted  4 years ago  in  Hotels, Restaurants and Dining, Loop List

4 MIN READ – One of the many perks of living in Chicago? The abundance of staycation options at your fingertips. Since you may not be able to get away to your favorite destinations right now, take a break and head downtown to the Loop to wine, dine and recline at some of the city’s top attractions, restaurants and hotels.


Hotel Essex 

With an exceptional downtown location, Hotel Essex offers luxurious rooms that include espresso machines, high speed Wi-Fi, and extraordinary views of Grant Park and Lake Michigan. You’ll be at the center of all the city’s most iconic activities, as Hotel Essex is only a short walk away from Millennium Park and the Museum Campus. If an afternoon on the Chicago River is calling your name — enjoy an exclusive discount on boat rentals from Chicago Electric Boat Company when you book the Sightseer’s Paradise Package.

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Kimpton Gray Hotel

The Kimpton Gray Hotel has everything you need to enjoy the perfect staycation. If you’re interested in finding a place to rest, relax, and recharge — look no further than the Spa Bathtub Escape package, where you’ll be spoiled with an assortment of bath salts, an eye mask, and your choice of wine, prosecco, or a DIY gin and tonic bar en suite while you unwind within the hotel's MTI Baths soaking tub. Afterward, head upstairs to the 15th floor to Boleo, the hotel’s rooftop restaurant and bar offering dramatic flavors and sultry beats of South America. 

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Staypineapple, an Iconic Hotel, The Loop

Ready. Set. Staycation!  Planning your dream Staypineapple staycation is easy and affordable. Reserve your room between now and September 7 and stay before October 2, and save an extra 10%. On top of the savings, Staypineapple offers plenty of other perks. Have a meal on them with a $20 Grubhub card, or travel with your best four-legged friend and forget about the pet fees. Staypineapple Chicago is purposefully located exactly where you want to be, so you can choose any number of safe social distancing things to do right outside the front door.  

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Renaissance Chicago Downtown

Located in the heart of the Loop and surrounded by the Theatre District, the Renaissance Chicago Downtown offers beautiful views of the Chicago River, lively bars, and a plethora of top-notch dining. If you are up for an adventure, the Chicago L train is located right outside the hotel’s doors, providing easy access to further explore the city’s unexpected experiences. The Renaissance Chicago offers something for family members of all ages, including a full fitness center, indoor pool, and memorable dining at Raised, an Urban Rooftop bar. Special weekend rates and packages are also available.

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With the city reopening, Loop restaurants look to invite diners to new and improved patios, allowing for properly socially distant dining experiences. Most restaurants also have curbside pickup and takeout options available for diners to take a taste of the Loop home with them. Check out our guide to the best places to dine (or takeout) on a beautiful summer evening.


Maggie Daley Park

Spend the day at Maggie Daley Park! The Park Pass includes one round of mini golf at the Chicago-inspired 18-hole course, scooter or roller blade rental to traverse on the quarter mile ribbon, and an opportunity to soar with the skyscrapers on a 3-minute trampoline bungee jump. Enjoy a beautiful stroll through the Lurie Gardens or a picnic in the 28-acre park. Dine al fresco or take it to-go at Rink Café. The Park Pass is $17 and can be purchased online or onsite. The pass includes $10 parking at Millennium/Lakeside Garage and is valid Thursdays and Sundays from noon-6 p.m., and Friday and Saturday from noon-8 p.m. through Labor Day.

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Shoreline Sightseeing 

A Shoreline Sightseeing Architecture River Tour makes an ideal centerpiece for a day or weekend in the city. Enjoy an award-winning, 75-minute tour led by one of Shoreline’s expert guides, plus close-up views and fantastic photo ops of landmark buildings lining the scenic Chicago River. With multiple departures from the Michigan Avenue Bridge (all Navy Pier tour operations have ceased for the 2020 season), it’s easy to find a time that works with your personal staycation itinerary. Check out their Loop Deal for a discount on adult Architecture Tour cruises.

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Wendella Boats

Wendella Boats is the original architectural river tour and cruise company in Chicago. Bask in the glow of the sunset with their iconic Sunset River Cruise, or go the scenic route with the classic Architecture Tour. Wendella is currently adhering to the strictest COVID-19 protocols with proper social distancing on boats, as well as safety and cleaning precautions. Tours depart from the Wendella Main Dock at 400 N Michigan Avenue and from the Wendella West Dock, located West of the Wrigley Building at the lower level of Kinzie and Rush.

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Chicago Architecture Center

The CAC River Cruise aboard Chicago’s First Lady is “The Architects’ Choice” and the #1 choice among TripAdvisor users. Enjoy a tour with your friends and family, and soak up the summer sunshine while hearing the secrets and stories behind Chicago’s riverfront buildings, as told by expertly trained CAC docents. With new safely distanced seating, space is strictly limited, so don’t delay—book today! Continue your exploration with a visit to the Chicago Architecture Center. Combo tickets include admission to the Center for just $5 (regularly $12). You’ll experience the world’s largest model of Chicago with more than 4,250 miniature buildings, discover world-famous skyscrapers with local roots, and explore Chicago’s unique neighborhoods. Plus, look for new models on display in the Drake Family Skyscraper Gallery. Discounted admission is valid up to seven days before or after your cruise. 

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Green Star Movement

Green Star Movement may not be hosting DIY classes, but they are still offering do-it-yourself fun, with DIY Mosaic Kits that people can purchase and mosaic at home. Kits cost $35 and include pre-cut pieces, a design stencil, glue, grout kit, and instructional guide. With several options, including a Chicago Flag serving tray, vases in blue or warm tones, a picture frame with a geometric pattern, a flower pot with a rainbow design, and a serving tray with a Black Lives Matter design (20% of profits are donated to Brave Space Alliance), family members of all ages are sure to enjoy a carefree, summer activity. All designs are beginner-friendly, and shipping is available in the Chicagoland area for an additional $10.

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August is National Family Fun Month and 360 CHICAGO offers a BOGO offer that allows you to bring a family of four up to the 94th floor of the John Hancock Center for as little as $25 (2 adults/2 kids). If you're a Chicago resident, you receive 50% savings on all ticket purchases throughout August. All guests may purchase one adult ticket to earn a free youth ticket (ages 3-11). Kids under 3 enter free. Grab a tempting gelato at BAR 94 where you’ll also find snacks, soft drinks and specialty cocktails and brews from some of Chicago’s favorites: Koval Distillery and Revolution Brewing Co.

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What’s open in the Loop?

From restaurants to shops, museums to public art, there are plenty of ways to enjoy a summer in the city. Don’t forget to pack a bag, apply some sunscreen, and grab your mask for some time #BackInTheLoop.

How to get to the Loop

No flight necessary for this trip. Here are all the best ways to get to the Loop.

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