3630 N. Clark St.
Perfect for:A fancy clubhouse sleepover after the Pearl Jam concerts
Cool upgrade:The schnazzy Marquee Suite (from $1,500) has panoramic windows overlooking the iconic Wrigley Field sign.
Tip:If you book directly but then find a lower rate elsewhere, the hotel will match the price and knock off 20 percent.
Cons:Even a nice hotel can’t stop the drunken debauchery outside in Wrigleyville.
Sophy Hyde Park
1411 E. 53rd St.
Perfect for:A culture-packed weekend
Cool upgrade:The 48 Hours in Hyde Park package ($628) includes two nights in a suite, admission for two to the Museum Campus South institutions, $25 credits for the onsite restaurant and local bookstores, a basket of treats, and parking.
Tip:Feel free to unplug. Each room comes with a record player and a vinyl collection featuring local musicians.
Cons:There’s no rooftop, so sidewalk dining at its restaurant, Mesler, will be your only alfresco option.
Moxy Chicago Downtown
530 N. La Salle Dr.
Perfect for:Uninhibited millennials
Cool upgrade:Book an Inner Circle room ($10 more) for deliberately intrusive views across a narrow courtyard into neighboring rooms.
Tip:Happy hour in the bar-like lobby includes drink specials, games, and a Zombie Taco bar.
Cons:Your neighbors aren’t the only thing on display—even the frosted shower stall juts into your room.
St. Jane Chicago
230 N. Michigan Ave.
Perfect for:A ritzy couple’s getaway
Cool upgrade:The upscale Tower, a swanky hotel-within-a-hotel that opens in September, includes 33 art deco suites and a “personal curator” (i.e., butler) who will walk your dog, stock your bar, and even fog you with a perfume from the likes of Hermès and Tom Ford.
Tip:Book a northeast corner room ending in “04” for the best views.
Cons:St. Jane’s 24th-floor rooftop bar is only available to guests staying at the Tower.