Chicago Athletic Association
Free to walk into. Check out Cindy’s because the view is astounding. The food is a bit pricy, but if you share with a friend it is reasonable. Also visit the second floor hotel lobby and game room. It feels like going back in time.
Shedd Aquarium
Offers occasional free days. Take the time to really watch the sea creatures. Look for the anaconda. He’s huge.
Chicago Art Institute
Offers occasional free days. Ranked as one of the world’s best art museums. Grant Wood’s American Gothic is one of the most iconic pieces in the collection.
Field Museum
Offers occasional free days. Sue is fun to pose with.
Jackson Park
Free. Large park south of the Museum of Science and Industry. Visit the Wooded Island to see examples of Japanese architecture and gardens. Stay out of the koi pond unless you are preventing littering.
Oriental Museum
Free. They do request donations for the chance to see rare artifacts. On the campus of the University of Chicago. See objects that Abraham, Moses, and Daniel would have seen.
University of Chicago
Free. The grassy lawn that runs through is the Midway from the 1893 World’s Fair. There's also some great bookstores in Hyde Park that you should totally check out.
Maggie Daley and Millennium Park
Free. Giant slides and equipment make you feel like a little kid again. Attend a free concert on the lawn get a photo with “The Bean.” Maggie Daley Park is the greatest play park ever for adults who wish they could still be children. I wouldn't recommend bringing very little children as it can be difficult to contain them and there are a lot of older kids running around.
Lincoln Park Zoo and Conservatory
Both are free. Visit the ape house. There was always ape family drama going on there.
Alfred Caldwell Lily Pool
Free. Three acres of ponds and small waterfalls right next to the zoo. Step in and you feel more like you’re at Walden Pond than in the heart of a large city.
North Shore Beach
Free. Bring a towel and a Frisbee. Relax.
Federal Reserve Bank of Chicago Money Museum
Free. Have your ID. See more than 3 million dollars in cash. Take home a free sample of Fed Shreds.
The Rookery
Free to walk into. Tour can be purchased online or in person. I would highly recommend the tour. On special days tours that go up to the library are available, but space is limited so plan ahead. Dark and foreboding on the outside, but beautifully light on the inside.
Chicago Board of Trade
Free to walk into. Fabulous example of Art Deco architecture. Visit the vault downstairs. Great and reasonably priced cafeteria downstairs as well.
Museum of Science and Industry
Occasional free days, but on those days the museum is usually packed. Great to have a membership. Take the WOW! tour that takes you behind the scenes.
John Handcock Building
Save up for a fancy meal at the Signature Room. It is on the 95th floor of the building and offers incredible views.
Sears Tower Skydeck
Cost. Not something to do repeatedly, but defiantly worth a visit once.
Oak Park
Suburb. Tour the Frank Lloyd Wright house and studio (cost). Wander and see the other houses Wright designed while working on the World’s Fair.
Chicago Shakespeare Theater
Located on Navy Pier. Anyone under 35 can get two tickets for $20 each.
Palmer House
Free to walk into. Tour the hotel lobby. The brownie originated here and one can still be purchased at the restaurant or in the lobby. It was a bit pricey and not the best brownie, but I still like saying I’ve tasted something that is original.
Wicker Park
Area within Chicago. Great food. Cool shops.
Wendella Boat Cruises
Cost. Tickets often available on Groupon. Great views of the city. I loved the architectural tour. Perfect for a warm day.
Michigan Avenue
Area in Chicago. Known as the Magnificent Mile there are many stores and restaurants. One of our favorites is the Grand Lux. Check out the Tribune Building. It has little chunks from famous structures around the world set into it.
Water Tower and Pumping Station
On the Magnificent Mile. Beautiful at Christmas. Only two buildings to survive the Great Chicago Fire.
Ghirardelli Chocolate
Near the Water Tower. Everyone who walks in gets a free chocolate square. Get a dessert to share with friends or don’t share. I won’t judge.
Chicago River
Enjoy a walk along the river or take a Water Taxi. The river is quintessential Chicago. The city reversed the course of the river. So Chicago. Take a boat ride through the locks out into Lake Michigan. Go downtown in March to see it dyed green. The link takes you to the "Friends of the Chicago River" page, but there is other information available elsewhere.
Anderson's Bookshop
Anderson's is an independent bookstore with multiple locations. They bring in excellent authors for events and do an excellent job of engaging with the public. Readers are encouraged to explore through books and other nerdy paraphernalia. Anderson's is reader's paradise.
Free to walk into. Check out Cindy’s because the view is astounding. The food is a bit pricy, but if you share with a friend it is reasonable. Also visit the second floor hotel lobby and game room. It feels like going back in time.
Shedd Aquarium
Offers occasional free days. Take the time to really watch the sea creatures. Look for the anaconda. He’s huge.
Chicago Art Institute
Offers occasional free days. Ranked as one of the world’s best art museums. Grant Wood’s American Gothic is one of the most iconic pieces in the collection.
Field Museum
Offers occasional free days. Sue is fun to pose with.
Jackson Park
Free. Large park south of the Museum of Science and Industry. Visit the Wooded Island to see examples of Japanese architecture and gardens. Stay out of the koi pond unless you are preventing littering.
Oriental Museum
Free. They do request donations for the chance to see rare artifacts. On the campus of the University of Chicago. See objects that Abraham, Moses, and Daniel would have seen.
University of Chicago
Free. The grassy lawn that runs through is the Midway from the 1893 World’s Fair. There's also some great bookstores in Hyde Park that you should totally check out.
Maggie Daley and Millennium Park
Free. Giant slides and equipment make you feel like a little kid again. Attend a free concert on the lawn get a photo with “The Bean.” Maggie Daley Park is the greatest play park ever for adults who wish they could still be children. I wouldn't recommend bringing very little children as it can be difficult to contain them and there are a lot of older kids running around.
Lincoln Park Zoo and Conservatory
Both are free. Visit the ape house. There was always ape family drama going on there.
Alfred Caldwell Lily Pool
Free. Three acres of ponds and small waterfalls right next to the zoo. Step in and you feel more like you’re at Walden Pond than in the heart of a large city.
North Shore Beach
Free. Bring a towel and a Frisbee. Relax.
Federal Reserve Bank of Chicago Money Museum
Free. Have your ID. See more than 3 million dollars in cash. Take home a free sample of Fed Shreds.
The Rookery
Free to walk into. Tour can be purchased online or in person. I would highly recommend the tour. On special days tours that go up to the library are available, but space is limited so plan ahead. Dark and foreboding on the outside, but beautifully light on the inside.
Chicago Board of Trade
Free to walk into. Fabulous example of Art Deco architecture. Visit the vault downstairs. Great and reasonably priced cafeteria downstairs as well.
Museum of Science and Industry
Occasional free days, but on those days the museum is usually packed. Great to have a membership. Take the WOW! tour that takes you behind the scenes.
John Handcock Building
Save up for a fancy meal at the Signature Room. It is on the 95th floor of the building and offers incredible views.
Sears Tower Skydeck
Cost. Not something to do repeatedly, but defiantly worth a visit once.
Oak Park
Suburb. Tour the Frank Lloyd Wright house and studio (cost). Wander and see the other houses Wright designed while working on the World’s Fair.
Chicago Shakespeare Theater
Located on Navy Pier. Anyone under 35 can get two tickets for $20 each.
Palmer House
Free to walk into. Tour the hotel lobby. The brownie originated here and one can still be purchased at the restaurant or in the lobby. It was a bit pricey and not the best brownie, but I still like saying I’ve tasted something that is original.
Wicker Park
Area within Chicago. Great food. Cool shops.
Wendella Boat Cruises
Cost. Tickets often available on Groupon. Great views of the city. I loved the architectural tour. Perfect for a warm day.
Michigan Avenue
Area in Chicago. Known as the Magnificent Mile there are many stores and restaurants. One of our favorites is the Grand Lux. Check out the Tribune Building. It has little chunks from famous structures around the world set into it.
Water Tower and Pumping Station
On the Magnificent Mile. Beautiful at Christmas. Only two buildings to survive the Great Chicago Fire.
Ghirardelli Chocolate
Near the Water Tower. Everyone who walks in gets a free chocolate square. Get a dessert to share with friends or don’t share. I won’t judge.
Chicago River
Enjoy a walk along the river or take a Water Taxi. The river is quintessential Chicago. The city reversed the course of the river. So Chicago. Take a boat ride through the locks out into Lake Michigan. Go downtown in March to see it dyed green. The link takes you to the "Friends of the Chicago River" page, but there is other information available elsewhere.
Anderson's Bookshop
Anderson's is an independent bookstore with multiple locations. They bring in excellent authors for events and do an excellent job of engaging with the public. Readers are encouraged to explore through books and other nerdy paraphernalia. Anderson's is reader's paradise.
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