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Planning your trip to Chicago and trying to figure out where to see the best views? Or wondering what uniquely Chicago things there are to do here and nowhere else? Read on for suggestions from a native Chicagoan and tour guide for the last 15+years. Have fun exploring!
where to go to get the best views & some uniquely Chicago things to do
Jay Pritzker Pavilion in Millennium Park
The photo above was taken at the Jay Pritzker Pavillion in Millennium Park while enjoying Bluesfest this past June. Bluesfest is an annual concert that I highly recommend to any blues music fan to put on your list. Three days of fantastic blues musicians, young & old, at three different stages. And did I mention that it is free? My new favorite performer is Melody Angel, a young local woman who really rocked it! And an oldie but a goodie Ronnie Baker Brooks did not disappoint. They also featured up & coming musicians & we happened to see Nick Alexander. Turns out that he is the son of longtime blues man Linsey Alexander, and he was awesome.
There are free concerts/movies from Memorial Day through Labor Day at the Jay Pritzker Pavillion in Millennium Park. Click here to read my guide on exploring the Loop. Also, if you want to take a self-guided tour, download the eAtlas app, and you can purchase my Art, Architecture & History, oh my! route. I’m also working on offering my tour routes on my blog so you can hire me to give you a tour in person. Stay tuned!
reflection in the Bean (aka Cloudgate)
Along with concerts at Millennium Park you have to go see the Bean. It is super cool at all times of day and during different seasons. I am in the park most days during the summer season, and I think it’s still pretty spectacular. No wonder it is the top photographed attraction in Chicago.
view of Millennium Park from Maggie Daley Park
Maggie Daley Park is the 20-acre kid-focused park just east of Millennium Park. Take the bridge (it looks like a snake from an aerial view) over to lots of fun activities like mini-golf, climbing walls surrounded by a skating ribbon, picnic groves, playscapes & more!
One of the best views of the city, hands down. Did you know Lake Shore Drive (LSD) used to run right through the Museum Campus? In the late 1990s, the northbound lanes were moved west to create the Museum Campus. All together in one spot are Chicago’s world-class museums, the Field Museum of Natural History, the Shedd Aquarium, the Adler Planetarium, and lots of green space for locals & tourists to enjoy. How to get here? Jump on a Divvy bike, take a water taxi, or a bus. Check out cta trip planner to help figure out the best way to see this gorgeous view. Click here to save up to 40% from CityPASS.
What brings this local to Navy Pier besides fireworks (Wednesdays & Saturdays), Venetian night, and the SOFA show (Sculptural Objects Functional Art)? The Original Rainbow Cone! Best. Ice Cream. EVER!
Er, uh, you know, the Sears Tower. I am obligated to say Willis Tower because I am a tour guide, and technically, that is its name, but I slip and call it Sears Tower a lot. Usually, I come here when touring around a group of students. Go check out the Skydeck. Recently they redid their exhibit space, and I hear it’s pretty cool.
The Skydeck at Willis Tower has a pretty spectacular view, but so does the 96th Signature Lounge at the John Hancock Tower aka 875 N Michigan. Go to the lounge, order a drink, relax & take in the view. Or you can go check out the TILT – 360 Chicago. FYI – I much prefer the lounge. Check here for hours.
view from Buckingham Fountain
The photo above was taken a couple of summers ago when I had family visiting from out of town. We usually go see a concert at Millennium Park, then head over to the fountain. Growing up on the southside, we used to pile in the station wagon on Sundays and head to Buckingham Fountain. Afterward, we would get a Rainbow Cone. Lots of fond memories.
view of Buckingham Fountain
Turn around, and the photo above is your view. Make sure you check out the fountain at night as well. Click here to learn more about Buckingham Fountain.
driving on LSD from the southside to downtown Chicago
You’ll see this view coming from the southside (Hyde Park) either by car or bike. The Lakefront trail is 18 miles long and runs along beautiful Lake Michigan. The trail is very popular in the running world and was where I trained for the Chicago Marathon (my first & last) a few years back. Not much of a runner anymore, but I do still bike along the path quite a bit. I try to bike once a week from my house to downtown, which is about 10 miles each way.
go to a rooftop
There are multiple rooftops throughout the city, from Cindy’s at the Athletic Association Hotel in the Loop to the Robey in Wicker Park. This view is from the Cerise (Virgin Hotel) in the Loop. It’s one of the less crowded rooftops with an amazing view of the Jewelers Building and Marina Towers. Definitely, something you should check out while visiting Chicago. Click here for a list of rooftops.
view from the Robey in Wicker Park
Wicker Park is just a quick ‘L’ ride from the Loop. Jump on the Blue Line (towards O’Hare) and get off at Damen. This is one of the most popular neighborhoods known to have some of the best restaurants, bars & shopping in the city. It also has many beautiful, historic homes. I plan on offering this route when I get my tours up on my blog to book. Stay tuned!
bike the drive
I’ve done Bike the Drive multiple times. It’s pretty cool biking LSD (Lake Shore Drive) without any cars. Bikers of all ages are welcome to ride as much of the 30-mile drive as you want and can join a post-trip festival in Chicago’s Grant Park afterward.
The 20th Annual is coming up on Sunday, September 4th, and benefits the Active Transportation Alliance. Active Trans is a non-profit advocacy organization working to improve conditions for walking, biking, and public transit throughout Chicagoland. Click here for details.
The photo above was taken from the Bird Sanctuary at Montrose Beach. One of my favorite summer activities is to ride my bike to Montrose and go SUPing (stand-up paddleboard). Lots of good fun & a great workout. You can also rent kayaks here as well.
north pond cafe
This is the view from my front yard when I lived in Lakeview. I think it captures our city motto Urbs in Horto – City in a Garden. I would run, bike, or walk along the Lakefront pretty much every day. Click here to read my blog post on what else to do while you are in the area. Perhaps, go see a secret garden?
nature boardwalk in lincoln park zoo
I took this photo above while killing time before a movie. Specifically, the summer screenings of the Chicago International Fim Festival that took place on Tuesday evenings at the Chicago History Museum, just a couple of blocks away. In July, they moved to Wednesdays at the Cultural Center in the Loop. All summer long, a film is shown from a different country every week, this year’s theme being Adaptation. I’ve seen three movies so far this summer that were quite good, and I hope to see a few more before it ends in September. Tickets are free, so you can reserve them online or just show up & see if they have availability. You can get details here. If you are a film buff, stay tuned for the Fall session of the Chicago International Fim Festival in October.
art on the mart
The Merchandise Mart was home to Marshall Field’s wholesale inventory, housed in this massive 4 million sq foot Art Deco beauty. It was owned by the Kennedys and had its own zip code. Now it houses luxury home interior showrooms and has a nightly projection show. Across the Riverwalk, on the north bank of the Chicago River, is known as Wolf Point. This, my friends, is where Chicago started out as a small trading post back in the 1770s. Interested in learning more? Download the eAtlas app, and you can purchase my Discover Chicago’s Near Northside route.
go boating on Lake Michigan
I am so lucky to have friends with boats. There’s nothing quite like spending an afternoon on beautiful Lake Michigan or watching the fireworks on a glorious summer evening.
take an architectural river cruise – at night
To get one of the best views of the city, take an architectural river cruise. There are multiple companies to choose from. Here is a link to help you narrow it down & to get a discount. The cruises are offered frequently throughout the day. My favorite time to take an architectural river cruise is the evening when the sun is setting and the city lights are coming on. If you are in town on a Wednesday or Saturday, chances are you will get the added bonus of seeing the fireworks from Navy Pier.
bike the 606
Bike the 606 (the Bloomingdale Trail) and explore the neighborhoods of Wicker Park, Bucktown, Humboldt Park, and Logan Square. Previously a busy train route, now much-needed green space for the residents of these neighborhoods. Click here for details.
I hope this guide on where to see the best views and uniquely Chicago things to do helped you plan your trip. I’m working on getting my tour routes up on my blog, so you’ll be able to book a tour with me soon. Stay tuned & have fun exploring!