Best things to do in Chicago

Written By Joseph Kelleher

Take an Architecture and True Crime tour! If you have already done that take the Murder Mystery tour!

Odds are you have already taken my tour the Architecture and True Crime tour, (if you haven’t here is a link) but have you taken my friends Murder Mystery Tour? Embark on a thrilling journey through Chicago’s Gold Coast. Play and interrogate as suspects, solving a gripping murder mystery.

Walk/bike along the Lakefront

The Lakefront is the best part of Chicago, in my opinion. It stretches the entire length of the city and beyond, over 26 miles of the Lake Michigan. I have spent a large part of my childhood on the lakefront, whether it be the beaches or the fun activities. It might sound strange, but alot of the beaches don’t even have sand. Hanging out on a concrete beach might sound weird, but its actually really fun!

  • Montrose Beach, I would argue the best spot on the lakefront. Never too crowded, with the largest beach, including a dog-friendly side, and of course Chicago’s hottest couple, Monty and Rose (rare Pipping Plovers who nest there) in their serene bird sanctuary. Just a little further south is the Clock Tower Cafe, one of my favorite spots in the city (They close on rainy days).

  • Belmont Harbor, by Boystown and Wrigleyville, this area is great if you don’t like sand because you can sunbathe on the giant concrete steps. If you like floaties this is the best spot as farther south they ban them. Also almost always will have space.

  • North Ave beach, while not as crowed as Oak Street, this place is usually packed. But its the one I go to by far the most for one simple reason. CHESS. You can find the Chess Pavillion, Chicago’s Washington Square Park. My friend Will goes there a lot, on a nice Saturday or Sunday your almost certainly going to see him, he is an animal at chess. Speaking of animals there is also the second biggest public zoo in the US just a 8 minute walk from there.

  • Oak Street Beach, The most convenient spot from the ending of our tour, but always the most crowded. If you are to go here, I would recommend the concrete over the sand because the beach is small and its a lot easier to find your own little space. Same goes for Ohio Street Beach a little farther south.

  • 31th Street Beach, Another beach that is usually crowded. But it isn’t that crowded on the water which makes it by far the best place for jet skiing. (plus the cheapest)

Check out the cool buildings

  • Chicago has a lot of cool buildings, but even cooler, you can go into a lot of them for free. When I was making the route for ATC I went into a lot of different buildings. I have decided to use my knowlege to create free interior archtecture tour routes. I have 5 potentenal routes you can take, starting with the financial district. P.S. Most buildings close on nights/weekends I will add in the times these routes are open, but 4 and 5 are definitely the best routes if its night/weekends. I also underlined the can’t miss buildings on each route.

  • About a 40 minute walk
    If you like old tall buildings this is the tour. After the Marquette building its a bit of a walk to the other three.

    • The Rookery – 209 S LaSalle St

    • Field Building (LaSalle National Bank) – 135 S LaSalle St

    • Wintrust Building – 140 S Dearborn S

    • Chicago Board of Trade – 141 W Jackson Blvd

    • Monadnock Building – 53 W Jackson Blvd

    • Marquette Building – 140 S Dearborn S

    • 311 South Wacker -311 S Wacker Dr

    • The Old Post Office - 433 W Van Buren St

    • The Art Institute of Chicago, 111 S Michigan Ave (Have to pay)

    • Palmer House – 17 E Monroe St

    • Sullivan Center (Target) – 1 S State St

    • Marshall Field’s / Macy’s on State – 111 N State St

    • Chicago Cultural Center – 78 E Washington St

    • Chicago Theatre – 175 N State St (have to pay/plan)

    • Nederlander Theatre -24 W Randolph St

    • City Hall – 121 N LaSalle St

    • Thompson Center – 100 W Randolph St (It isn’t open yet but when it is, definitely worth checking out.

    • Harold Washington Library Center – 400 S State St

    • Fine Arts Building – 410 S Michigan Ave

    • Auditorium Building – 430 S Michigan Ave

    • Congress Plaza Hotel (Gold Room) – 520 S Michigan Ave

    • Chicago Hilton – 720 S Michigan Ave

    • Chicago Athletic Association Hotel – 12 S Michigan Ave

    • Hotel Inter-Continental – 505 N Michigan Ave

    • Carbide & Carbon Building – 230 N Michigan Ave

    • LondonHouse Rooftop (London Guarantee Building) – 85 E Wacker Dr

    • Chicago Motor Club – 111 W Wacker Dr

    • Merchandise Mart – 222 Merchandise Mart Plaza

    • Drake Hotel – 140 E Walton Pl

    • Ambassador Hotel – 1301 N State Pkwy

    • 3 Arts Club Café at RH Chicago – 1300 N Dearborn Pkwy

Catch a Cubs game at Wrigley Field

  • Second oldest stadium in the MLB, Wrigley is packed with history. The coolest part of Wrigley Field though is the stadium doesn’t end once you leave. The whole neighborhood has been built around it for over a century. There really isn’t anything quite like it in the US.

Watch an Improv show at Second City!

  • My friend Sarah has her own show. Check her out at the Improv bachelorette.

Joseph Kelleher
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Lincoln Park/Old Town