STAY Peninsula Chicago (108 E. Superior St.; 312/337-2888; $445+) has been rated by Conde Nast Traveler as the No. 1 luxury property in the world -- and yes, this is where celebrities like Madonna and Jennifer Aniston stay whenever they are in Chicago! Each room offers opulent, tech-driven digs that let you control everything from lighting to "Do Not Disturb" notices from a bedside console. The hotel's spa offers swimming and/or a massage. Within the hotel you'll also find The Bar, with fireside divans, fine dining at Avenues, or dim sum at Shanghai Terrace.
In the Kimpton line-up is the Hotel Monaco (225 N. Wabash; 866-610-0081; $169+).
The Monaco's unexpected amenities include "tall" rooms for those vertically over-challenged and accommodations for your accompanying pet. Additional rooms features include "meditation stations," wide deep window seats with comfortable cushioning, a CD stereo and complimentary (temporary) goldfish. The intimate lobby invites pleasant guest interactions with lots of comfy chairs, Art Deco flourishes, and a glowing fireplace. The Kimpton Hotel Group offers a slew of enticing 'Women's Packages', including the Diva Package and the Divine Diva.
A Sister's Place (4753 North Broadway #918, North Side; 773/542-9126; $55+)
Closer to social activities, A Sister's Place has been renting rooms in an artist's flat for 20 years. Two rooms are available in this comfortable Uptown apartment, next to an El stop and many stores. Women only. Open year round.
EAT Topolobampoand Frontera Grill (both at 445 N. Clark St; 312-661-1434; Topolobampo $24-39, 5 course chef's tasting menu $75, Frontera Grill $16-27)
Topolobambo and its more casual sibling cook up the best Mexican dishes north of the border. Both sides offer authentic, gourmet regional Mexican cuisine, courtesy of prolific cookbook author, TV chef and master Mexican chef, Rick Bayless. Although the crowd is mostly straight, these places are a must-try for any visiting foodie. It's big name frocks or a suit and tie if you want to be seated in Topolobampo. The dress code is not an issue at the just-as-delicious Frontera Grill.
A favorite eatery, close to Andersonville, is Tweet (5020 N. Sheridan Rd; 773-728-5576; $5-25), Big Chicks bar owner Michelle Fire's latest labor of love. During the day, Tweet Let's Eat is a brunch spot serving causal breakfast to hung-over gay boys and lesbian soccer leagues. By night, this diner is transformed into Tweet Le Soir, an upscale restaurant with prix fixe dinners during the week.
PLAY/MEET Bars Star Gaze (5419 N. Clark St., Andersonville; 773-561-7363; $6-11)
An ethnically eclectic, easy-going neighborhood lesbian bar with pool tables. Groups of enthusiastic sporty dykes cluster in corners or lounge within viewing distance of various TV screens in this warmly lit venue with 70s bar decor. Occasional theme nights, live shows and some food served. Stock up on beer battered mushrooms, chili, pizza or veggie quesadillas. Friendly. Go with friends or alone to make new ones. Closed Monday.
Lost and Found (3058 Irving Park Road; 773-463-7599) Chicago's oldest lesbian bar is another constantly popular neighborhood women's bar, open six nights a week (closed Mondays), attracting the "over 35s" to their pool tables.
Club Escape (1530 E. 75th St; 773-667-6454) This mostly African American-frequented mixed gay/lesbian bar has DJs and a hot dance floor. Women flock to take their place on it Tuesdays and Thursdays.
T's (5025 N. Clark Street, Andersonville; 773-784-6000)
A friendly, mixed (lesbian/ gay/ trans) bar and restaurant with a super hot retro 80s night for women every Tuesday.
Clubs Chix Mix Productions (various venues; 773-583-5049)
Responsible for the delights of the ilk of the Black Bra Party, Tanked, and Party Like a Rock Star, Chix Mix concoct slick, sexy, high-energy circuit parties for up to 1,000 Chicagoland women from their 20s to 40s (men as guests) in venues in the city and suburbs.
Temptations Nightclub (10235 W. Grand Ave.; 847-455-0008) is one of Chicagolands? largest lesbian clubs. Burlesque stars occasionally, pool is the main attraction on Wednesday, karaoke on Thursday and Sunday nights and DJs on Fridays and Saturdays.
EXTRA Sex Early to Bed (5232 N. Sheridan Rd; 773-271-1219)
This lesbian-owned, transgender-friendly erotica outlet, Chicago's first women-owned sex shop, is well equipped with toys, such as neat vibrapen or lipstick vibes, and erotic gifts. Frequented by people of all genders and orientations. They also organize "pleasureware" parties. Closed Mondays.
Stores Women and Children First (5233 N. Clark St; 773-769-9299 or 888-923-7323)
This women-owned and run institution is an excellent lesbian/feminist bookstore in Andersonville (close to Tomboy, see above) and a great place to browse books, music and clientele. Open late Wednesday through Friday. Wheelchair accessible.
Quimby's Queer Store (1854 W. North Avenue, Wicker Park; 773-342-0910)
An excellent source for comics and alternative reads, as featured in Go Fish.
RELAX Thousand Waves Spa for Women (1212 W. Belmont; 773-549-0700)
An enticing women-only Japanese style spa offering massage (including hot stone and pre-natal), herbal wraps, eucalyptus steam bath, spa, dry sauna and more. Kimonos, towels, shampoos and tea all provided. Thousand Waves also run a Martial Arts and Self Defense Center.
Lincoln Park (along Lake Shore Drive, beginning at North Ave)
Running close to five miles along the edge of the city on Lake Michigan, this beautiful park is one of the nicest public spaces in the city. Inside are a lovely botanical garden, a zoo (the Lincoln Park Zoo, one of the country's oldest), and a few decent public beaches. Rent a tandem on Navy Pier and coast along with your loved one.
Be sure to follow Out Traveler on your favorite social platform
DON'T MISS THE OUT100 SPECIAL 3 DAY MARATHON STARTING NOVEMBER 24TH!
Journey through the year’s influential Out100 – the most iconic and long-standing celebration of LGBTQ+ icons and allies – in a 1-hour television special spotlighting the LGBTQ+ people shaping the world today.