travel to do list for chicago, il

An obsessive travel list for Chicago, Illinois

Sweet home, Chicago. Where the small-town midwest feel meets world class museums, craft beer and sports teams that keep things interesting. Anytime of year–though probably not January through St. Patrick’s Day–Chicago is a beautiful place to be.

Chicago is a town of neighborhoods, and each neighborhood has its unique vibe and heritage. There are of course the museums, Michigan Ave and Sears/ Willis Tower, but there is so much more to Chicago and the people who call themselves Chicagoans then you’ll find on a postcard in Walgreens. I implore you to venture out and experience the microcosmos.

Every summer in Chicago, there are neighborhood festivals. If you are lucky enough to be in the city during the pretty-months, you may want to see which neighborhood is hosting the block-party.


Get a CTA card and ride around on the ‘L. Everyone uses the ‘L; it’s great and a lot easier to understand than NYC’s subway system.

Uber and Lyft are both very popular in Chicago.

where i have stayed

  •  Gateway Hostel is in a younger neighborhood, but it’s cool. Close to one of the local universities. It’s a little dingy for my taste, but free breakfast.
  • International Hosteling is a great place, and I typically stay here because it’s in the thick of downtown and makes getting on any L line very easy. However, it’s not close to a lot of trendy restaurants or bars and you’ll miss a truer neighborhood experience staying so close to Michigan Ave and the business district.
  • Holiday Jones. It’s away from the tourist areas, but it’s really cool. Lots of great bars and taco places, and it’s easy enough to get to O’Hare Airport and to get to The Loop (downtown) via the Blue Line. This is my favorite spot.

tourist attractions

Chicago is a great city, with plenty to do inside and outside.

  • Art Institute of Chicago, which is sometimes voted better than the Louvre.
  • Grant Park with Cloud Gate (the Bean) and Buckingham Fountain
  • The Shedd Aquarium
  • The Museum of Science of Industry is SO COOL with tuff from the moon landing and the Apollo missions, plus my favorite: a creepy exhibit of human fetus in different stages of life.
  • The Field Museum is fantastic. If you don’t want to spend the money, at least go into the lobby and see Sue, the largest, most complete dinosaur skeleton ever found.
  • Architecture boat tour on the Chicago River
  • Skip Sears Tower/ Willis Tower; it’s not worth it. Go to the Hancock Building’s Signature Lounge on the 95th floor and order a cocktail. Same price and a MUCH better view. Ladies, the best view of Chicago is said to be from their women’s restroom.
  • Navy Pier is a thing, but I think skippable.
  • The Madhouse on Madison for a Blackhawks or a Bulls game.
  • Wrigley Field for the Cubs
  • Cellular One Field for the White Sox
  • Deep dish pizza is a Chicago staple. I suggest Gino’s East on Superior and Michigan Ave or Pequod’s on Clybourn and Webster Ave.
  • Chicago Style hotdog at Portillo’s

streeterville + river north neighborhoods

Streeterville–think Michigan Ave–and River North is a great place for rooftop fun, skyline views and great foodie-finds. This area is more expensive, so be prepared to spend the extra cash when you chose to eat, drink and party here.

  • Seminary Co-Op Bookstore near Chicago University is a beautiful, tight-cornered bookstore.
  • City Winery on the river walk is good for wine and a great way to spend a nice day outside.
  • London House Rooftop Bar
  • Virgin Hotel’s Rooftop
  • POPs for Champagne
  • The Berkshire Room inside the ACME Hotel has an intimate, speak-easy vibe to it.
  • Three Dots and a Dash for a fun atmosphere and Instagramable drinks.
  • Eatly is an Italian grocery store with several micro-restuarants. It’s a foodie’s dream.
  • Siena Tavern for great Italian.
  • River Roast for a bluesy brunch on the weekends.
  • The Purple Pig for small plates and great wine.
  • Sunda for sushi fushion.
  • Paris Club for french food. I once saw George Lucas here, so it has his intergalactic approval.
  • Public House for a casual night out.
  • Fado’s Irish Pub
  • Redhead Piano Bar for some great music and cool vibes.
  • The Hangge Up for those nights that you just don’t want to end… and they don’t have to until 4am.

gold coast + old town neighborhoods

Though still a bit pricey, this area is at least less touristy. You will be able to go to a happy hour, meet a few of Chicago’s finest and visit some locally-own shops.

  • North Avenue Beach is the bro-tastic beach area with volleyball courts.
  • Spice House for an amazing shopping experience for spices.
  • Old Town Oil
  • Second City or UP Comedy Club
  • Old Town Pour House
  • Wells on Wells
  • Old Town Social

lincoln park + wrigleyville neighborhoods

These neighborhood have a youthful, more energetic lifestyle. With a university nearby and America’s most bro-tastic sports neighborhood a few L stops away, there is always fun to be had.

  • Powell’s bookshop is one of the largest in the country, I believe.
  • Cafe Ba-Ba-Reba for small plates and great sangria.
  • Homeslice for pizza and a lazy meal with friends.
  • Summer House for Americana food.
  • Melrose Diner is 24 hours
  • Glazed and Infused for donuts! Maple bacon… enough said.
  • Lincoln Park Zoo is free, and during the Christmas Season, you can see the Zoo Lights!
  • Bro-out in Wrigleyville. It’s night next to the Cubs baseball field, Wrigley, and there is always dancing, drinking and crazy happening someone along Clark Street at night.
  • Sluggers has a piano bar and batting cages upstairs, and a blue-blooded American club downstairs.
  • Cubbie Bear is a great place to watch the game or catch some live music, whatever is the flavor for that evening.
  • Irish Oak to get thing ridiculous.
  • John Barleycorn if you want to dance (and are prepared to elbow the boys that grind-up on ya).
  • Murphy’s Bleachers for a low key pre-game drink.
  • Sidetracks, on Sunday afternoons, plays show tunes into the night. It’s a fantastic Sunday Funday; all of Halsted street is.
  • Big City Tap is sometimes called “Big Shitty” because it’s a 4am bar.
  • Trader Todd for karaoke and laughs.

uptown + lincoln square + andersonville neighborhoods

These neighborhoods venture north of the Chicago-party, and are therefore a little bit slower and family oriented. However, if you venture to these neighborhoods, you won’t be disappointed by what you find.

  • Hopleaf has the best beer selection in the city. It’s a bit out of the way, but it’s my favorite place in the city to go hang out. And the food is amazing!
  • Baker & Nosh is in my old hood. If you go to Baker & Nosh on the weekend, they have croissants that will make you weep.
  • Fork has yummy food.
  • Chicago Brauhaus for a Das Boot of beir. The annual Mayfest is also held here.
  • Carroll’s Pub
  • The Green Mill for some world-class jazz.
  • Tweet for brunch.
  • Bad Apple for excellent burgers.
  • Montrose Beach is larger and more family friendly. If you just want to hang out for the day, this beach is better than North Ave.

wicker park + wicker park neighborhoods

This is the hipster area with lots of great coffee shops, tacos shops and trendy bars.

  • Wormhole Coffee is awesome.
  • Myopic Books
  • Big Star Tacos
  • Small Cheval for a great hamburger; it’s the pop-up shop for Au Chavel (see below).
  • ChopShop has live music.
  • Mindy’s Hot Chocolate has fabulous fried chicken followed by homemade marshmallows in your hot chocolate.
  • Beauty Bar has dancing!

the streets near fulton + randolph

Chicago was commonly referred to as the “Bread Basket of the Midwest.” The grain, livestock, vegetables and fruits from further west, poured into Chicago for market and distribution. Fulton and Randolph Market was the area for this. Even today, you can still see the wide boulevards that survived as evidence to this industry. And upholding it’s history, this area is a foodie’s dream come true.

  • Au Cheval doesn’t take reservations and they are always busy, but I swear it is the best burger I have ever had in my entire life. Go early, like 4:30 pm, go for brunch around 10am, or go, put your name down, and have a drink at another place nearby.
  • Girl and the Goat is just delicious.
  • SoHo House is a cool place to go hang for awhile. You can also have a tea here.
  • R&M Champagne has great oysters.
  • Parlor Pizza Bar has a bloody mary bar on the weekends.
  • Bar Siena is yummy, American food.
  • Duck, Duck Goat for fancy Chinese food.

oak park area

If you like American literature and/or architecture, I suggest you venture out to Oak Park. It’s where Ernest Hemingway grew up and where several Frank Lloyd Wright houses live.

  • Ernest Hemingway Birthplace
  • Unity Temple Restoration Foundation
  • Pleasant Home

breweries in chicago

  • Goose Island Brewery
  • Lagunitas Brewing
  • Haymarket Pub and Brewery
  • Half Acre Beer
  • Revolution Brewing

times to visit chicago

  • March for St. Patrick’s day (the city dyes the Chicago River Green!)
  • Summer months for neighborhood festivals
  • For Lollapalooza in August
  • For Blues Fest in June

other sources

About MollyKoe

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