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weekend in chicago train

How to Do a Weekend in Chicago

Wondering what to do in the Windy City? Here’s how to do a weekend in Chicago.


The Virgin Hotel Chicago is all about making your Chicago experience inviting, from the second you walk in to the moment you fall asleep. Chicago is the first Virgin Hotel property in the world, and the hotel certainly lives up to the brand’s expectations. On property, you’ll find a wine and coffee bar adjacent to the lobby, Two Zero Three, serving specialty drinks like a lavender latte. Also adjacent to the lobby is the property’s main restaurant, Miss Ricky’s, serving funky American fare and a killer brunch. On the second floor, you’ll find a swanky lounge and bar area, called The Commons Club, as well as some meeting rooms and spaces. On the top two levels of the hotel you’ll find an amazing gym; Upstairs, which is a concert space with a private outdoor heated deck; and a full bar and lounge on the roof, called Cerise, that has both in- and outdoor spaces (and super comfy lounge chairs).

In-room amenities include bathrobes, a separate vanity area with mirror, minibar and fridge (with normal prices!), on-demand TV, an ergonomically designed bed frame, plenty of lights and outlets, a desk area for working, free Wi-Fi, turndown service, and large open windows overlooking the Loop area. The Virgin is also pet-friendly (no weight restrictions), with a stout ceramic guard dog designating a pet-friendly room.


While the hotel’s amenities, restaurants, and bars make it hard to leave, you’ve only got a weekend in Chicago, so get out there! After you check into the hotel, grab a coffee and head over to Millennium Park (about a seven-minute walk) and see “The Bean” and other outdoor sculptures. Then walk down the street to the Art Institute of Chicago and check out its collections and visiting exhibits. For dinner head back to the hotel and eat at Miss Ricky’s, then head up to The Commons Club, Cerise, or Upstairs if you so desire.


Get an early start on the Chicago Architecture Foundation River Cruise and learn all about the Second City through the history of its architecture. After the 1.5-hour tour, walk to RPM Steak for a steak, a salad, or (my favorite!) a truffle burger, and then make your way to Goose Island Brewery for a tasting and tour. Head back to the hotel for a quick recovery and make your way to the Fulton Market District for dinner and drinks. You really can’t go wrong here, so pick a restaurant based on which cuisine you’re craving. If you’re up to it, head to the famous tiki bar Three Dots and a Dash for a nightcap.


Order room service from Miss Ricky’s for brunch and then head out to either Navy Pier or Lincoln Park Zoo, depending on your interest, followed by a final view of Chicago from the Skydeck on top of the Willis Tower. Head back to the hotel before you depart and have yourself an “Upside Down Tea Party” (yes, that means alcoholic hot or cold tea) at The Commons Club. The tea drink options change seasonally and will surely be one of the most unique cocktails you’ll ever taste.

Beyond a Weekend in Chicago

If you’re spending more than just a weekend in Chicago, here are some extra things to do.

Walk around the trendy neighborhoods of Lincoln Park and Wicker Park Bucktown and explore their shops, restaurants, and bars. Catch a game at Wrigley Field if you have time or take a tour if you’re visiting in season. And, if it’s warm out, head to any of the public beaches along Lake Shore Drive for some fun in the sun.

Bars & Restaurants

Museums & Attractions

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Ashley spent a weekend in Chicago courtesy of Virgin Hotels ChicagoFollow her on Twitter and Instagram for more advice on travel hacks and destination ideas.

Editor’s note: This story was originally published in 2016. It has been updated to reflect the most current information.

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