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Chicago Travel Guide: Where to Stay, What to Eat, and More

While the combination of cold weather and indoor attractions remaining closed may not result in an 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 the city to assemble a travel guide to Chicago to make the most of your time outdoors.

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Where to Stay

In need of a getaway? A local vacation can help feed your wanderlust. Explore these ideas for inspiration, then start planning your own Chicago experience. When traveling in Chicago, don’t forget to book an overnight stay in a hotel. If you’re not a local and it’s your first time visiting Chicago, the travel to Illinois’ from your chosen temporary home can take some time. That’s why we’ve also taken into consideration the time and distance it takes to go from point A to point B.

Best Luxury: Thompson Chicago

When in Illinois, Thompson Chicago is a sophisticated yet cool, timeless yet edgy, and energizing yet comforting place to be. 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 collections are inspiring. The furnishings in the rooms mirror the hotel’s public areas. Showpieces include indigo sofas and cabinets, whimsical contemporary art, and herringbone carpets. The bathrooms feature large walk-in rainfall showers, and many of the rooms have separate soaking tubs.

  • Time: 23 min by car
  • Distance: 14 miles

Book from $161 at Booking.com.

Best Modern: Hotel Julian

Hotel Julian, named for St. Julian, the patron saint of hospitality, provides a hip, modern 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 with high ceilings and sleek, trendy designs. The location of Hotel Julian is unmatched, as it places you steps away from Millennium Park, Navy Pier, Riverwalk, Monroe Harbor, and Grant Park.

  • Time: 22 min by car
  • Distance: 12 miles

Book from $96 at Booking.com.

Best Airbnb for Couples: Artist’s Loft in The West Loop

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. This loft is definitely worth staying in when you make your Chicago trip a reality.

  • Time: 24 min by car
  • Distance: 15 miles

Book from $83 at Airbnb.

Best Splurge: The Langham

If you want your stay in Chicago to be an unforgettable one, you might as well go all out with your accommodations. The Langham is the place to be if you want a lavish haven that will give you the utmost comfort. The stylish and modern interior also makes it a picturesque hotel. Not only is it beautifully decorated, but it’s also located near Michigan Avenue’s Magnificent Mile. You can fully appreciate what downtown Chicago has to offer when you stay at The Langham.

  • Time: 38 min by car
  • Distance: 13 miles

Best Location: Chicago Athletic Association

Situated in the heart of Chicago, the Chicago Athletic Association is the place to be. If you fancy a rooftop bar where you can see Millenium Park in its full glory, you should definitely consider this luxury hotel. You can also experience world-class dining and amenities. The rooms also have an elegant, vintage feel, where both modern technology and classic woodwork collide.

  • Time: 27 min by car
  • Distance: 12 miles

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 where you can take a fine sip of craft beer. (Of course, restaurants are still counting on takeout and delivery to get them through the pandemic months, so don’t forget to order out, too.)

Aba

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. 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, either.

  • Best for Brunch and Dinner
  • $$

Browse the Menu

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.

  • Best for Lunch and Dinner
  • $$

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Giant

Pre-COVID times, Giant operated as a tiny restaurant. During COVID, Giant turned into a food truck that stations itself in parks all over Chicago. Regular menu items such as 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.

  • Best for Dinner
  • $$

Browse the Menu

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 for things you can still do to make the most out of your Chicago trip.

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 your 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, Illinois, 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 night, plus live entertainment from local musicians. Private heated igloos are also available for lunch and dinner.

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, Illinois, 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 birdwatch. With the fire table blazing and the moon and stars swirling overhead, this is the ultimate mini-getaway.

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