16 things I love to do in Chicago

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 Chicago is a beautiful place to be. It is a town of neighborhoods, and each neighborhood has its unique vibe and heritage. There are of course the museums, Michigan Ave, Millennium Park 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 at Walgreens.

This is a pretty difficult post for my write because I really could go on forever about the best things to do in Chicago.

1. chicago in the summer

Not only is the weather better in the summer, Chicagoans are better in the summer. With the exception of St. Patrick’s Day, Chicagoans seem to hibernate after Christmas until the weather is warm enough to venture outside without having to wrap yourself in a down comforter. But Chicago in the summer is glorious!

You can take boat out on the lake for Instagramable view of the skyline or enjoy a neighborhood festivals/ block parties any weekend. There are baseball games and outside, rooftop dining options and good vibes to be had. Millennium Park was a summer film series and the Shedd Aquarium hosts Jazzin’ at the Shedd. You can go on an architectural tour via river boat or kayak you way through the city via the Chicago River.

2. on st. patrick’s day, we dye the river green

For whatever reason, Chicago likes to affiliate itself to Ireland and for one week a year, everyone you meet in Chicago has a good chance of claiming Irish heritage and/or dropping the term “Chirish” into casual conversation. The Chicago River is dyed green–a yearly check for leaks schedule opportunely around St. Patrick’s Day–the south side throws a fantastic parade and any Irish pub anywhere in the city has may play host to river dancers.

The bro and I enjoying St. Patrick’s Day and the green river.

3. christmas time

Michigan Ave is twinkled with Christmas lights, Marshal Fields is looks like every department store in every Christmas movie you’ve ever seen, the Lincoln Park zoo hosts Zoo Lights–a free festive event–and for those young and crazy enough to participate, Wrigleyville hosts the Twelve Bars of Christmas pub crawl (affectionally called TBox) every December.

2. taking the cta

Get a CTA card and ride around on the ‘L. Everyone uses the ‘L; women in fur coats and the homeless, college students and suits on their way to the loop. The CTA is a great way to get around, is a lot easier to understand than NYC’s subway system and, in most cases, is a lot faster than a cab.

Uber and Lyft are both very popular in Chicago.

3. it has the great museums in the world

I can’t choose a favorite museum in Chicago, so please don’t ask. It’s a multi-way tie between:

  1. Art Institute of Chicago, which is sometimes voted better than the Louvre.
  2. The Museum of Science of Industry, which is SO COOL. It has stuff from the moon landing and the Apollo missions, plus my favorite: a creepy exhibit of human fetus in different stages of developement.
  3. The Field Museum, which 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.
  4. The Shedd Aquarium, especially their summer Jazzin’ at the Sheedd series.

For $106, you can get a Chicago City Pass, which will get you access to several tourist highlights around the city, including all the museums I mentioned above.

Boating around Lake Michigan.

4. getting a good look at the city

Skip Sears Tower/ Willis Tower; it’s not worth it. Instead, I suggest you 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. I won’t argue with this sentiment.

Any rooftop restaurant along Michigan Ave will also give you a great view of the city, my favorite being Cindy’s Rooftop Restaurant.

5. being a chicago fan

Chicago is in the midwest, which means passionate sport fans live in the city. There is baseball, football, basketball, hockey and soccer to enjoy. For Cubs games, even if you won’t want to pay for tickets, are still fun to enjoy in Wrigleyville at one of the local bars. Or you can pay a premium price and watch from a luxury rooftop around the field. If soccer is more your jam, find a bar provides a Pub to Pitch bus to Toyota Stadium to watch the Chicago Fire Play.

Blackhawks’ Stanley Cup Parade through the Loop, 2015.

6. eating the chicago foods

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 is a thing other people are crazy about. Just never-ever ask for ketchup when in Chicago.

7. 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.

Tourist attracting include most of the museums, Grant Park with Cloud Gate (the Bean) and Buckingham Fountain, and Navy Pier (but I think this is skippable).

Here are my favorite eats and drinks in Streeterville and River North:

  • 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.

Take an architectural tour on the Chicago River.

8. 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. Nearby North Avenue Beach is the bro-tastic beach area with volleyball courts.

My favorite stop in the Gold Coast and Old Town are:

  • 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

Chicago is sometimes known specifically for its Second City comedy club. Second City lives in Old Town and is always a hilarious time. Be sure to plan ahead, though.

9. lincoln park + wrigleyville neighborhoods

Lincoln Park and Wrigleyville 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.

Below is the laundry list of stores, restuarants and bars I enjoy in this area:

  • 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 open 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.
  • Lincoln Park Zoo
  • Botanical Garden

Chicago Botanical Garden

10. uptown + lincoln square + andersonville neighborhoods

These northern neighborhoods are a safe distance from 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. Some of my favorite places in the city hide in the northern neighborhoods. They are:

  • 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!
  • 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.

11. wicker park + bucktown neighborhoods

These hipster areas come with lots of great coffee shops, tacos stops and trendy bars. My favorite haunts are:

  • 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 606 is a great order doors space fit for walking, running and riding a bike.

SoHo in Chicago

12. 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.

13. 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

14. breweries in chicago

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

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!

Playing with “The Bean” in Millennium Park.

15. nerding out on literature

There are several book shops and museums around the city the will make every fellow nerd smile. Here are some of my favorite stops:

  • Harold Washington Library
  • Seminary Co-Op Bookstore near Chicago University is a beautiful, tight-cornered bookstore.
  • Powell’s bookshop is one of the largest in the country, I believe.
  • Myopic Books
  • Stony island arts bank
  • Writer’s Museum

16. free tours

I am always a fan of free walking tour no matter were I am. When I have the time, I try to go on the free walking tours in Chicago to learn something new about the city I love so much. There are some pretty interesting tour, one following the history of the mob in Chicago!

staying for cheap in chicago

  • 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.

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