1. What would your perfect day off look like? 

A. Restaurant hopping and catching up on the Tribeca Film Festival picks, with three to seven outfit changes throughout the day 
B. A double-header at the Art Institute and the Museum of Contemporary Art, followed by drinking a glass of wine in the park while watching someone try to parallel park their giant car into a tiny space. Poetic, kind of. 
C. Wearing footie pajamas and watching a Ken Burns documentary turned up so loud that the neighbors file a noise complaint
D. Picnicking by the lake. Skipping rocks on the lake. Putting my feet in the lake. Becoming one with the lake. That should take a full day. 

2. Hotel soaps. What’s your plan for these?

A. Using them normally? 
B. Idly stacking them until I accidentally create a work of art that projectiles me to fame 
C. Peeling off their wrappers and laminating   them so that I have a piece of history in case something notorious happens at this hotel one day 
D. Hoarding them. They are nice, and what if I’m, like, shipwrecked and need to wash my hands? 

3. What’s your vacation motto? 

A. Pictures or it didn’t happen. 
B. Ceci n’est pas une margarita on the beach. 
C. Vacation is for making memories — I mean histories. Vacation is for making histories. 
D. Rum for me, milady! Keep away, scurvy! I don’t normally talk like that, but it is making me stand out here at Jimmy Buffett’s Margaritaville. 

Photograph by David Massey/DMP Productions LLC

If you picked mostly A’s: Nobu Hotel Chicago

The long-delayed Hollywood icon finally made its debut in Chicago last summer as both a restaurant and a hotel. It’s the spot for purveyors of the newest trends, and also for fans of owner and rising young actor Robert De Niro. Stay in one of 115 minimalist, Japanese-influenced rooms, including the Zen Deluxe Suite, which has a teak soaking tub that overlooks Randolph. From $359 a night. 155 N. Peoria St., West Town

Courtesy of 21c Museum Hotel Chicago

If you picked mostly B’s: 21c Museum Hotel Chicago 

This spot just off the Mag Mile features a contemporary art museum with rotating exhibits that’s open seven days a week. Each of the 297 rooms also includes original artwork, so if you’re feeling more like staying in bed and watching HGTV all day, that’s fine — you can still technically say you’re taking in culture. From $120 a night. 55 E. Ontario St., Near North Side

Courtesy of Pendry Chicago

If you picked mostly C’s: Pendry Chicago 

Housed in the 1929 art deco Carbide & Carbon Building, this hotel fuses the historic with the luxe. The higher the floor, the better the view from your sleek room. But depending on your priorities, the best panorama of all can be had from either the 24th-floor rooftop deck or the ground-level Venteux, the Parisian-inspired restaurant from Michelin-starred chef Donald Young that has an oyster-packed raw bar. From $220 a night. 230 N. Michigan Ave., Loop

Photograph by Mike Schwartz Photography

If you picked mostly D’s: Sable at Navy Pier 

Named after a navy training ship from World War II, the first hotel on Navy Pier is nautically themed: Weathered brass and shipbuilding materials cover the interior, and floor-to-ceiling windows showcase the lake. Plus, Navy Pier should be at least partially reopened in June, so there are plenty of ways to tire out your kids, put them to bed early, and go have some fun yourself at the hotel’s tapas restaurant, Lirica. From $199 a night. 900 E. Grand Ave., Near North Side