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

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

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

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

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

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

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 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

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

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

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

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

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

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

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

Lincoln Park Botanical Gardens

Lincoln Park

The north-side of Chicago's version of Garfield Park Conservatory. Right next door to Lincoln Park zoo. Rooms full of orchids, palms, ferns and much more.

  • Park
  • Other

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

Macy's

Downtown

This famous American department store is situated in Chicago's historic Marshall Fields building. A festive place to visit during the Christmas holidays with a...

  • Store

Montrose Point

Uptown

Right off the lakefront near the Uptown neighborhood, Montrose Point is home to a bird sanctuary and affords one of the best views of Chicago's skyline. Great...

  • Walking
  • Park
  • Natural Attraction