Jay Pritzker Pavillion
Downtown
If you're into music or any outdoor performance, you've got to attend something, anything, in Millenium Park at the Jay Pritzker Pavillion. Spread out a blanket...
- Performing arts
- Park
- Cultural & Historical
- Architecture
Promontory Point
Hyde Park
This human-made peninsula in the Hyde Park neighborhood is best enjoyed with some take-out food, chatting with friends around one of the designated bonfire...
- Other
- Park
- Natural Attraction
Ravinia Festival
Highland Park
Check out Ravinia's calendar of events while you visit Chicago, especially if you're visiting for more than a week. This elegant, outdoor music venue is ideally...
- Park
- Performing arts
Leather Archives & Museum
Rogers Park
One would never assume a leather/BDSM museum existed on this quiet, tree-lined street in Rogers Park. Leather Archives & Museum includes a collections library, a...
- Other
Boystown
Lakeview
This North Side Chicago neighborhood, official East Lakeview, is home to one of the more lively LGBTQ communities in the US, filled with an eclectic selection of...
- Architecture
- Food & drink
- Neighborhood
Chicago River Architecture Cruise
Downtown
This tour provides a historical guided tour of Chicago's notable skyscrapers while cruising along the famous Chicago river in Chicago's First Lady boats. Full bar
- Architecture
- Water fun
Field Museum
Museum Campus
The Field Museum is one of the most visited museums in Chicago. Located near the Shedd Aquarium and Adler Planetarium, most people make a day out of visiting all...
- Museum
Adler Planetarium
Northerly Island
This lake front astronomy museum is located at the tip of Northerly Island and next to the famous Chicago Shedd Aquarium. Check their calendar of events for
- Other
- Museum
Andersonville Galleria
Andersonville
A two-floor retail market comparable to an outdoor artisan market, Andersonville Market is the place to find local crafts. The Galleria is filled with over ninety...
- Market
Art Institute
Downtown
This is THE most well-known art museum in Chicago. It is home to many of Georgia O'Keefe's paintings and there is now a new modern wing. There are no...
- Museum
- Art
Chicago Cultural Center
Downtown
This downtown historical building is often overlooked by tourists. Formerly Chicago's library in the early 1900s, it now hosts free concerts, art exhibits,...
- Cultural & Historical
- Art
- Architecture
Chicago History Museum
Lincoln Park
A small, information-packed museum where visitors go to get the full scoop on Chicago's early history. Near the Lincoln Park and Old Town neighborhoods which are...
- Museum
- Cultural & Historical
Chicago Riverwalk
The Loop
This public waterfront walk gives you a whole new perspective of the city. Still under construction, slated to be completed In 2016, the river walk is...
- Walking
Green Mill
Uptown
The green mill in the Uptown neighborhood, is a historical landmark and noteworthy jazz club in Chicago, found an easy block from a red line EL train...
- Performing arts
- Cultural & Historical
Lincoln Park Zoo
Lincoln Park
Chicago's city zoo is free and open to the public all year round. Visit the Zoo Lights exhibit during winter months for a festive, holiday light show and crowds of
- Zoo
Museum of Science & Industry
Hyde Park
Chicago's Museum of Science & Industry is located on museum campus near the south-side Hyde Park neighborhood. The emphasis here is on interactive exhibits for...
- Cinema
- Museum
Steppenwolf Theater
Lincoln Park
Tucked away in the Lincoln Park neighborhood, this well-known non-profit theater operates year-round and offers unique events on their calendar. Although it...
- Performing arts
Tulip
Andersonville
This women-owned, local company offers a comfortable sex shop experience with an emphasis on healthy, environmentally-friendly toy materials. Offers "how-to"
- Specialty Shop
Alamo Shoes
Andersonville
An Andersonville staple since 1973, Alamo is a must-visit, old-fashioned shoe store with name brands like Dansko, Crocs, Sorel and Clarks. Extremely helpful and
- Store
Bobby's Bike Hike
Streeterville
Bobby's Bike Hike offers a variety of neighborhood and lakefront bike tours during spring and summer seasons. These tours are notable for taking you off the typical
- Bicycle
- City Tour
Bobby's Tike Hike: Kid's Edition in Chicago
Streeterville
While Bobby's Bike Hike offers a plethora of adult-catered bike tours, this bike tour specifically caters to the abilities of children ages 10 and under. Perfect for...
- Zoo
- City Tour
Brown Elephant
Andersonville
While this resale shop is typically the place locals get good deals on furniture, it's also a good place for those visiting to find quirky, thrifty clothes and...
- Specialty Shop
Eataly
Streeterville
An innovative New York style, Italian marketplace and eatery that is highly praised. A variety of mini markets to choose from with seated dining or take-out options....
- Market
Foster Beach
Lincoln Park
Foster Beach isn't exactly an LGBT destination, but it's high on the local's list of low-key, clean, accessible, white sand city beaches. Expect families and...
- Public beach
- Water fun
Frank Lloyd Wright Home and Studio Museum
Oak Park, IL
Explore this architectural landmark on the outskirts of Chicago in historical Oak Park. Several tours offered daily under $20 a person of this famous prairie-style...
- Museum
Garfield Park Conservatory
East Garfield Park
Recently restored, Garfield Park conservatory is fun to visit all year long, but especially during Chicago's winter months when locals visit to pretend they're...
- Other
- Park
Henry Gerber House
Old Town
A National Historic Landmark since 2015, the Henry Gerber House was home to the German-born founder of the Society for Human Rights, incorporated in Illinois as the...
- Cultural & Historical
Holstein Park Pool
Bucktown
This outdoor pool is perfect for an afternoon outing when it might be too hot for the beach. Amenities for young children, including playground, kiddie pool and...
- Public beach
- Water fun
Kathy Osterman Beach
Edgewater
Formerly known as Hollywood Beach, currently known as "gay beach", Kathy Osterman beach is the most well-known LGBTQ-friendly beach in the city. While the...
- Public beach
- Water fun
Kayak Chicago
Kayak through the Chicago river and its outskirts! Kayak Chicago offers guided group and private tours, classes, rentals, sunset and city nightlight paddles....
- City Tour
- Water sport & adventure