Who Your old college buddies. The grunge band you started as sophomores did well on the frat scene, then fizzled. Your buds begged for a reunion tour, but you bought them Lolla tickets instead.
Where W Chicago Lakeshore, 644 N. Lake Shore Dr.; 312-943-9200, whotels.com. From $299.
Amenities The contemporary W will appeal to your pals’ groovy side with W-branded CDs in-room and a DJ in the lobby (dubbed “The Living Room") on weekends.
Bonus Kanye West, last year’s Lollapalooza headliner, stays here when he’s in town.
Who Your fussy cousin, who’s eight months pregnant, and her husband. She’s always won all the attention; now she demands it.
Where Four Seasons Hotel Chicago, 120 E. Delaware Pl.; 312-280-8800, fourseasons.com/chicagofs. From $470.
Amenities Luckily, the staff at the Four Seasons is used to pandering and does something extra for mothers-to-be with its “Expecting You” package (with rooms, rates start at $530). Expectant moms get a complimentary manicure when they book a pregnancy massage at the hotel spa, free breakfast in bed, and discounts at area kids’ boutiques.
Bonus Homemade ice cream delivered to her guestroom door (side of pickles, anyone?)
Who Your sports-frenzied brother-in-law and his pals, here on a pilgrimage to see the Cubs.
Where Best Western Hawthorne Terrace, 3434 N. Broadway; 888-860-3400, hawthorneterrace.com. From $159.
Amenities The go-to hotel for out-of-town Cubs fans (the secret’s out, so book a few weeks in advance), it’s clean, compact, and minimally decorated. But your bro and his cronies probably won’t spend too much time inside, unless they’re basking in a Cubs win in the sauna or whirlpool.
Bonus Twenty bucks buys 24 hours’ worth of parking in the next-door garage, with in-and-out privileges.
Who Your foodie friends from San Francisco who want a taste of Chicago’s good life. They call it a “gourmet-cation.” You call it panic as you scramble to make reservations at top restaurants.
Where The Peninsula Chicago, 108 E. Superior St.; 312-337-2888, chicagopeninsula.com. From $525.
Amenities A bar and four upscale restaurants, including the four-star Avenues, where James Beard Award nominee and “Iron Chef” competitor Graham Elliot Bowles dishes up wonders like pheasant pot-au-feu.
Bonus The Lobby’s Friday and Saturday night all-you-can-indulge-in chocolate buffet.
Who Your soccer-mom sister and her four hyperactive kids. She’s hoping a weekend in Chicago will give the kids some culture (and lengthen their attention span long enough to avoid a tantrum at Garrett’s Popcorn).
Where Essex Inn, 800 S. Michigan Ave.; 312-939-2800, essexinn.com. From $99.
Amenities A ten-minute walk from the Museum Campus, the Essex Inn also offers package deals with the Field Museum, Sears Tower Skydeck, the Art Institute of Chicago, and more.
Bonus A rooftop atrium with a huge swimming pool overlooking Grant Park.
Who Your history-buff, architecture-obsessed uncle. When he’s not glued to the History Channel, he exchanges war stories with old friends.
Where Hotel Burnham, 1 W. Washington St.; 312-782-1111, burnhamhotel.com. From $209.
Amenities Rehabbed and rechristened as a hotel in 1999. Look for some preserved interior elements such as heavy wooden room doors and quatrefoil metalwork in the stairwell.
Bonus The hotel provides MP3 players loaded with ten-minute spiels about the building’s history. Al Capone’s dentist’s office was in what’s now room 809.
Who Your shopping-obsessed girlfriends, here to hit boutique after boutique. They’re on a mission to blow a month’s salary at Helen Yi and Hejfina. You’re their enabler.
Where Wicker Park Inn, 1329 N. Wicker Park Ave.; 773-486-2743, wickerparkinn.com. From $115. Apart-ments from $165.
Amenities A six-room bed-and-breakfast where the owners, Laura and Mikky Wright, are as laid-back and as much fun as the neighborhood. For something more private, your girls can rent one of two apartments, each equipped with a full kitchen.
Bonus The Wrights also own the nearby Alliance Bakery, and their Continental-style spread at the Inn is rife with oven-fresh pastries.
Who Your dad, who retired and went all “Parrot-head” on you. Now it’s nonstop Carnival cruises, sandy beaches, and margaritas.
Where Hotel Indigo Chicago Downtown Gold Coast, 1244 N. Dear-born St.; 866-521-6950, goldcoastchicagohotel.com. From $189.
Amenities The decidedly un-business feeling of the lobby-from its plucky green-and-blue décor to those beachy Adirondack chairs-is also reflected in the rooms. Each looks like the interior of a mini Nantucket vacation house.
Bonus Oak Street Beach is just five minutes away on foot-and the lobby bar serves tapas and piña coladas on command.
Photography: West © Allstar Picture Library / Alamy, Bowles Courtesy Of The Peninsula Chicago, Bag By Megan Lovejoy, Hotel Photography Courtesy Of The Hotels Edit Module