![room at the W hotel in Chicago](/wp-content/archive/images/2007/May 2007/hotels.W.jpg)
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.
![the Four Seasons Hotel in Chicago](/wp-content/archive/images/2007/May 2007/hotels.fourseasons.jpg)
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?)
![a room at the Best Western in Chicago](/wp-content/archive/images/2007/May 2007/hotels.bestwestern2.jpg)
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.
![hotel room at the Peninsula Chicago](/wp-content/archive/images/2007/May 2007/hotels.peninsula.jpg)
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.
![a hotel room at the Essex Inn in Chicago](/wp-content/archive/images/2007/May 2007/hotels.essexroom.jpg)
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.
![Hotel Burnham in Chicago](/wp-content/archive/images/2007/May 2007/hotels.burnham.jpg)
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.
![Wicker Park Inn in Chicago](/wp-content/archive/images/2007/May 2007/hotels.WickerPark.jpg)
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.
![Hotel Indigo Chicago Downtown Gold Coast](/wp-content/archive/images/2007/May 2007/hotels8.jpg)
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