The Manual may earn a commission when you buy through links on our site.

A Social-Distance-Friendly Staycation Travel Guide to Chicago

While the combination of cold weather and indoor attractions remaining closed may not result in the most ideal situation, there are still ways to enjoy a city’s vibrant art scene, diverse restaurants, and famed architecture during this time. We’ve searched across Chicago to assemble a staycation guide to make the most of your time outdoors.

Related Guides

Where to Stay

In need of a getaway? A local staycation can help feed your wanderlust. Explore these ideas for inspiration, then start planning your own Chicago experience. To get the full vacation experience, don’t forget to book an overnight stay in a hotel.

Thompson Chicago

Thompson Chicago is sophisticated yet cool, timeless yet edgy, energizing yet comforting. This stylish boutique hotel has an urban industrial feel that starts in the lobby. The décor is filled with textures of leather, velvet, and flannel. The art and book collection is inspiring. The furnishings in the rooms mirror the hotel’s public areas. Showpieces include the indigo sofas, whimsical contemporary art, herringbone carpets, and indigo cabinets. The bathrooms feature large walk-in rainfall showers and many of the rooms have separate soaking tubs.

Book from $161 at

Hotel Julian

Hotel Julian, named for St. Julian the patron saint of hospitality, provides for a hip, modern, lifestyle hotel experience. Julian’s classic Chicago architecture and spaces filled with natural light are inviting to any type of guest. Every room gives off major urban energy vibes with their high ceilings and sleek, trendy design. The location of Hotel Julian is unmatched as it places you steps away from Millennium Park, Navy Pier, the Riverwalk, Monroe Harbor, and Grant Park.

Book from $96 at

Best Airbnb for Couples

What better way to escape than by staying in an airy and bright artist’s loft? The 1,250-square-foot industrial space flaunts exposed brick walls with ironwork elements. This custom-designed space has beautiful high ceilings with ample natural sunlight pouring in through the windows.

Book from $83 at AirBnB.

Where to Eat

This winter, restaurants in Chicago are finding creative ways to extend outdoor rooftop season. From igloos to heated rooftops, there are still a number of outdoor dining options available. Of course, restaurants are still counting on takeout and delivery to get them through the pandemic months.


Aba offers Mediterranean-inspired bites like whipped feta, falafel, and warm, fluffy pita bread. Diners can also find larger dishes like short rib shakshuka and pan roasted diver scallops with Turkish figs and black lentils on the menu as well. Reserve a private greenhouse or warm up around the heaters and fire pits on the rooftop. If you’d prefer to order in, all dishes are available for pickup or delivery. Don’t skimp on the cocktail kits.

Beatnik On The River

This boho-chic riverfront oasis makes you feel like you’ve been transported to an exotic destination. Beatnik On The River claims to have gotten its inspiration from the 1950s and 1960s. Dishes offered are from around the world. The colorful tile, ethnic daybeds, and fringe umbrellas make you want to lounge around all day. Patio heaters and clear coverings have been added to keep diners warm. Takeout is an option as well.


Pre-COVID times, Giant operated as a tiny restaurant. During COVID, Giant is a food truck which stations itself in parks all over Chicago. Regular menu items such as their saffron tagliatelle are still available for takeout, but items such as scrumptious pizza, burroti (a burrito wrapped in roti bread) and doughnuts can be devoured from the food truck. The best way to follow the food truck is via Instagram.

What to Do

As the pandemic wears on, it can be hard to stay upbeat. That’s why you need some enjoyment now more than ever. Fun still exists, we promise, you just have to look a little harder. Here are a few suggestions of things you can still do in Chicago.

Create Your Own Chicago Art Crawl

Attractions and activities may be closed, but Chicago’s street art scene is still present and free to take in. Start you crawl in Pilsen, where there are numerous vibrant murals throughout the neighborhood and in alleys. Don’t miss the Hector Duarte Studio. Make your way to Logan Square, then to Concord Music Hall and take a photo in front of the “Greetings From Chicago” mural nearby. Finish your personal street art tour at Rogers Park where there’s a stretch of art along the Red Line wall path.

Indulge in High Tea

Craving some hot tea, pastries, and clotted cream? Head to the Drake Oak Brook to enjoy afternoon tea, complete with sophisticated service and lite bites. The charming property is located on the outskirts of Chicago in Oak Brook, IL, just over a 20-minute drive from the city. If you plan on going, check out their calendar of events beforehand as they sometimes offer wine and paint nights and live entertainment from local musicians. Private heated igloos are also available for lunch and dinners.

Unplug in a Treehouse

You won’t have to drive far to get to an oasis; a half hour to be exact. The Enchanted Garden Treehouse in Schaumburg, IL is the perfect outdoor escape during restless times like these. Besides being able to relax in the hot tub with a good book (or a drink), you can also lawn bowl in the yard or play tennis at the nearby tennis court. Snowshoe rentals are available at the nature center down the street. If you’re really all about getting in touch with nature, the area offers amazing opportunities to bird watch. With the fire table blazing, and the moon and stars swirling overhead, this is the ultimate mini-getaway.

Editors' Recommendations