Things To Do In Chicago since I moved to Chicago in 2005 and lived in the South Loop until embarking on our RTW journey.
We grew to really love the city and try to impress upon everyone we meet what a great place it is to visit and live.
Chicago is visited by almost 30 million tourists every year.
Undoubtedly, the best time to visit is during the summer.
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Things To Do In Chicago
The parks are green and filled with bikers and families picnicking, there are festivals nearly every weekend, boats are scattered across Lake Michigan, you can find the best views and Chicagoan’s are friendlier having emerged triumphant from another long, harsh winter.
This is not Los Angeles– automobiles are not required.
Regardless of how you arrive, you’ll be able to get around using the public transit system.
Riding the train is part of daily life in this city, and you will fit right in with the locals.
The elevated train system (called the “El”) is over 100 years old and is a sight to see itself.
The tracks make a loop in the city center before branching out to the many neighborhoods.
You can easily travel from one side of the city to the other and even to a few suburbs– all for only $2.25.
You can’t beat that.
The Chicago Transit Authority (CTA) has a great trip planner to help you find your way, and you can also see the El lines on Google Maps.
The new bus tracker system will let you know if you have time for one more Old Style.
You can even pull it up on your smart phone!
Be a Tourist – Things To Do
It’s okay to do touristy things in Chicago.
Tons of people from the suburbs and Midwest come to the city for that exact reason.
Join the masses.
There is a reason 30 million people visit each year!
The summer festivals in Chicago are enjoyed by everyone.
I really love our many music festivals (Jazz, Blues, Celtic, Latin, Gospel, Lollapalooza, etc.).
Most of these festivals occur in Grant Park, so you can’t miss them.
If you are in the city on a weekend, head to the Park and you’ll most likely run into some kind of event.
They are free to enter, but you’ll pay a high price for food and beer, especially at the massive “Taste of Chicago” at the Fourth of July.
Check out ExploreChicago.org for the schedule of events.
Millennium Park, the Magnificent Mile, and Navy Pier are among the top tourist attractions, but Millennium Park tops our list.
The park is suspended over an unsightly commuter train yard, and you’ll want to check out the ever changing modern art.
The highlight is the Pritzker Pavilion designed by renowned architect Frank Gery.
You’ll see locals with picnic baskets discretely enjoying wine or beer, spreading across the massive lawn.
Checkout some nice
You’ll also want to gaze into the Cloud Gate (aka The Bean) for hours and watch kids splashing in the Crown Fountain on a hot day.
The Art Institute of Chicago is directly South of Millennium Park and also worth a visit. Entry is free of charge on a designated evening (usually Tuesdays) in the summer.
Check with the museum to be sure.
There can be quite a line to get in on free admission days, so get there early.
The Magnificent Mile can be reached on foot from Millennium Park.
This stretch of Michigan Ave (from the Chicago River north to Oak Street) is known for it’s shopping, nightlife, ritzy condos, and architecture.
Coach, Tiffany, Chanel, Bebe, Ghiradelli, and Water Tower Place (our massive shopping mall) are all along the way.
There are some historic buildings on the Magnificent Mile as well like the Wrigley Building, the Tribune Tower, and the old Water Tower.
Navy Pier is also popular, but I say skip it.
It is essentially a big tourist trap and shopping mall…except on a lake.
Clark and I avoid this place unless we are seeing a movie at the iMAX theater.
You can take a high speed boat ride from the pier or just walk around and people watch.
The Pier isn’t all bad though.
Every Wednesday and Saturday evening, there is a fireworks show.
If you decide to visit, prepare yourself for screaming kids and the sweaty masses.
Rather than the speed boat tour, I highly recommend the architectural boat tour by Wendella on the river.
The guides really know their stuff and the views from the water are beautiful.
Chicago has the best architecture in the United States, and this tour is very informative.
Chicago Pizza and Hot Dogs
You can’t visit Chicago without trying a famous deep dish pizza.
Chicago deep dish pizza consists of a thick crust, inlaid in a round cake-like pan about an inch and a half deep, filled with lots and lots of cheese, meat, and veggies.
The best known and most frequented pizza joint is Giordano’s.
However, this is not the favorite of many locals.
I highly recommend Lou Malanati’s instead.
We think the crust is better and they really pack their pizza full of ingredients instead of using loads of cheese as a filler.
There are two locations that are easily accessed with public transportation from the Loop.
The South Loop location can be reached by taking the Red Line to the Harrison stop.
The River North location can be reached on the Brown Line Merchandise Mart stop.
At Lou’s we always get a small “Malnati Salad” and “The Lou” with sausage and a root beer.
I can only finish about a slice and a half, so don’t order too much!
Then, there is the Chicago Style hot dog.
The classic Chicago Dog is an all-beef frank, boiled, on a steamed bun (preferably with poppy seeds) and topped with fresh onions, green relish, pickle, tomato, mustard, one or two hot peppers, and celery salt.
No ketchup! (If you ask you may be scolded or ridiculed.)
There are endless number of places to get a dog in Chicago, mostly in the neighborhoods.
There are very few street vendors downtown and they won’t be serving up high quality dogs.
Here are a few hot dog places that are reachable from the loop on public transport
Chicago Hot Dog Restaurants
Local chain that serves up a good dog.
You’ll find a couple of locations in the city.
This place on Clark St. is a favorite for late night snack.
The workers are known for being rude and insulting.
Flub a Dub Chub’s: family run joint in Lakeview.
Good dogs! (and burgers too)
Jim’s Original Hot Dog:
Near the Medical district just west of the South Loop, this place has been serving up dogs for decades.
You can also get a great polish sausage with grilled onions.
This place is the only frozen custard in the city and also happens to have a great Chicago Dog.
Go there for both.
Eat Deep Dish Chicago Pizza Like a Local
There is much more to Chicago than pizza and hot dogs, however.
There are some great neighborhoods where you can get a pretty eclectic mix of high quality foods.
You’ll have to go a bit outside of the tourist zones for some of these treats, but it is worth it!
Hot Doug’s is an encased meat emporium and not a great place for vegetarians.
Doug grills up some great creations with exotic meats (elk, ostrich, pheasant, and foie gras) gourmet toppings, and interesting sauces.
He also does a great, simple, Chicago Dog.
You’ll wait in line for an hour or more in the summer, so be prepared.
But, it is worth it.
You’ll want to go on a Friday or Saturday when he makes the fries with duck fat.
Sounds strange, but I promise you’ll love it.
When we go with a group of friends, we usually each get our own dog and a few to share.
Work, family, kids…those are just ways to kill time between trips to Hot Doug’s.
Superdawg is another Chicago institution.
The iconic hot dog figures on top of the restaurant are well-loved by Chicagoan.
It’s been around since 1948.
This drive up joint puts a little twist on the Chicago Dog, but it is a definite favorite for locals.
Grilled onions, spicy mustard, pickled tomatoes, and crinkle cut fries are their specialty.
They also have burgers and great shakes and malts.
Devon Avenue is where you’ll find great Indian and Pakistani food.
It’s a LONG way north on the Red Line or you can drive.
It is absolutely worth the trip.
The food is cheap and oh so delicious.
The street is lined with restaurants, spicy smelling markets, and shops selling beautiful saris.
Pilsen is the place to go for some great, cheap Mexican food in the city.
This area is known for it’s Hispanic inhabitants.
You can find great street tacos and tamales as well as really affordable “sit-down” type restaurants.
The pink line will take you there, or you can drive.
Greek Town is definitely on the tourist radar, but well worth it.
Take the blue line to Halsted.
We recommend Greek Islands where you’ll get the signature flaming saganaki with a loud “Opah!” from the crowd.
If you want a quick bite, then just grab a gyro at a corner joint.
Rainbow Cone has the most unique ice cream cone in the city.
This layered cone is a blend of chocolate, strawberry, orange sherbet, Palmer House (their special creation), and Pistachio.
To get to the original location that is celebrating it’s 80th year, you’ll need to drive.
Public transportation will take you to some areas of the city that I would not suggest going on your own.
Luckily for tourists, there is now a downtown location at the corner of State and Lake, right under the El tracks, near the Chicago theater.
Comedy and Entertainment
Chicago is known for it’s high quality Improv Comedy.
Heading out for dinner, drinks, and a late night comedy show is a favorite weekend activity for Chicagoan’s.
I suggest heading to Improv Olympic, Comedy Sportz, or Second City.
Some of the best comedians (think John Belushi, Gilda Radner, Mike Meyers, Tina Fey, Steve Carell, to name a few) came from the Second City stage.
All three have great shows, performing long-form improv as well as short scenes and sketches.
Some even perform improvised musicals, which are amazingly done and very entertaining.
When Clark and I first moved to Chicago, we frequented Comedy Sportz at least once a month and were never disappointed with the quality of the show.
The wonderful nature of Improv is that it’s new every time!
There is so much more to say about the city we love, but this is a good start.
You could spend months, even years discovering the hidden jewels of this great place.
After living there for five, we just barely scraped the surface.
Hopefully our insight will help make your trip there a memorable one!