Life and Travel Hacking Blog

The Ultimate List of Things to do While Visiting Chicago

I travel a lot and one of the most common questions I get from fellow travelers is- “What should I do / see / visit while in Chicago?” I put together a post of my favorite things to do in the city and hopefully share some insights only a local would have.

Finding Local Events

Timeout Chicago and Choose Chicago websites are awesome to see whats going on in Chicago, I find the reviews on Timeout to be pretty spot on as to what actually expect at the event. During Chicago in the summer there is always a street fest, live music or some sort of activity to check out.

Things to Do

  • Summer Dance – free dance lessons then a few hours of dancing in Grant Park downtown
  • Architecture Tour – the boat tours are legendary
  • Millennium Park Concerts (make sure to bring a bottle of wine, snacks and blanket- also recommend getting their early for good seats)
  • Museums- Field Museum, Science and Industry, Art Institute, Shedd Aquarium and the Planetarium. There are other museums in Chicago you can check out but these are the main ones and the first three are staples of the city.
  • Beers to Try- Goose Island 312, Green Line Gossamer and Three Floyds’ Gumballhead
  • Breweries – Half Acre, Lagunitas, Hopewell Brewery,
  • Baseball- Cubs Game is always a ton of fun. The local insiders tip is to go to one of the many bars near the stadium to enjoy a few local beers, then after first pitch walk out to talk to the ticket scalpers (corner of Sheffield and Addison has them every 3 feet and only works if they aren’t playing well).
  • Brewery Tour- Goose Island tour is cool, it costs $10 and you get a cool pint glass a tasting of 6 beers at the end. Revolution, Half Acre and dozens more offer tours, check out this extensive list.
  • Funky Tours- Chocolate Tours, Cupcake Tours, Ghost Tour, Gangster Tour, Food Tour and even a Weird Tour.
  • Fun Experiences – Check out Dabble to take things like Knife Throwing or Glassblowing while in town.
  • Blues Music- Kingstons Mines, B.L.U.E.S. – they are both across the street from each other, various specials like students get in free during the week or pay cover at BLUES on Sunday and get into Kingston Mines for free the same night.
  • Summer Events – Jazzin at the Shed, First Fridays at the MCA and the dozens of Summer Street Festivals check Timeout as their is one every single weekend during summer.
  • Millennium Park- The “Bean” and the water faces art is really cool to see in person. Impressive venue for concerts and if you have kids make sure to walk over the Maggie Dailey Park.
  • Beaches- North Ave beach is packed on any warm sunny summer day in Chicago, make sure to check out the cover bands at Castaways (bar on the beach, rated one of the top beach bars in the world).
  • Lincoln Park Zoo and Conservatory- awesome zoo within the city and the conservatory has plants from all around the world, you will feel better with all the fresh oxygen you get checking out the exotic plants
  • Tall Buildings- John Hancock and Sears Tower (now called Willis Tower) both are worth doing for the view on a clear day. The trick for the Hancock is to not go to the skydeck but the Signature room on the 95th floor. Ask to sit by the window and you can order a round of drinks for about the cost of going 2 floors up.
  • Drinking – People in Chicago really enjoy drinking, pretty much you can find a busy bar any night of the week. If you are going out stick to bars in Gold Coast, River North, Lincoln Park, Wrigleyville and Wicker Park (yes bars are all over the city, but this is where locals tend to hangout)
  • Comedy – Second City is considered the top rung of comedy in this town, many of the SNL stars get their start with their group. If standup is what you prefer, Zanies is awesome.
  • Active lifestyle- Rock climbing at Maggie Daily Park or Brooklyn Boulders. Run / bike / rollerblade along the lake year round on a great path that goes for miles and miles (watch for ice in winter)

Favorite Neighborhoods

  • Lincoln Park – Armitage and Sheffield intersection – (Young, fun, 20-30’s) for nightlife you can go for drinks to Kellys Pub, Mcgees Tavern, State or Kinkades. For food check out Devil Dawgs (late night), Mcgees Tavern, Homeslice, Earl’s, Sweet Mandy B’s (desert), Lou Malnatis (pizza), Nookies Too (breakfast)
  • River North – (late 20’s – 40’s) Hubbard and Clark St is a good intersection to start at, walk either way on Hubbard. Many world class restaurants and bars. You will likely have an awesome meal at any of these RiverRoast, Frontera Grill, Bottlefork, RPM, Quartino’s, Beatrix, Sunda, Doc B’s and Joe’s Seafood.
  • Gold Coast – Rush St and Division, is kind of a tourist trap but these bars can be a lot of fun. Late night on Friday or Saturday with most of them open till 5am.
  • Wicker Park for delicious food check out Jerry’s Sandwiches, Mahalo, Piece Brewery, Lillie’s Q or Big Star. Tons of awesome bars at North Ave and Damen intersection. Brunch at Bongo Room on the weekends.
  • Wrigleyville- Clark Street and Addison Intersection – try to visit during a Cubs game to fully understand how crazy the neighborhood gets. Clark street is lined with bars and active on the weekends even when the Cubs are not playing.

Food (Chicago favorites)

  • For a beef sandwich- Portilios – $8-15 good for lunch or dinner, order is with sweet or hot peppers, also ask for it “wet” (the dip the sandwich). If you are adventurous order the Chocolate cake shake.
  • For a steak- Gibsons – fantastic steakhouse, very old school, recommend dressing up a bit- smells like old money when you walk in. TangoSur is BYOB and in a neighborhood.
  • For a deep dish pizza- Lou Malnatis – I recommend ordering The “Malnati Chicago Classic”. Pequod’s is another solid option.
  • For the best burger in the world- Kuma’s Corner – local tip is to get there right at 11:30am for lunch when they open, or else you may be waiting a while for one of their famous burgers.
  • Breakfast – Beatrix, Uncle Mike’s, Ann Sathers, Wildberry
  • Sushi – Sushi Dokku, Tanoshii, Radio Anago, Sushi San, Arami or Yozu

Getting Around

Finally the last tip is to buy a multi-day pass on the CTA (Chicago Transit Agency) which will give you unlimited rides on the buses and trains in the city. They sell them in 1,3,5,7 and 30 day increments. It is super easy to catch a cab in most neighborhoods anytime of day and in most cases they can be pretty cost effective if you are in a rush. Apps to catch a ride- Uber, Via and Lyft. But with that said sometime the train is much faster during rush hour (before and after work).