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The Best of the Windy City

August 24, 2023 /

Whether you’re heading to Chicago to run the marathon or you’re planning to do a little shopping on the Magnificent Mile, our recommendations for the best of the Windy City will help you know where to go, what to do, and even better…what to avoid while you’re there!

First up…let’s talk food

Where to go

Il Culaccino

Walking distance from McCormick Place, Il Culaccino is a great escape from the pace of the Convention area. Not only is the food is excellent, they have a great patio to enjoy on a warm day AND it is decorated with pictures from mob movies! Who wouldn’t like a little al dente pasta while looking at Al Pacino?

Grilled Calamari
Spaghetti & shrimp
Image of an outdoor patio with wood rectangular tables and red leather padded chairs. There are trees around the patio and round lights hanging overhead.
The patio
Image of the a soffit with large pictures from gangster movies. On the right is Joe Pesci and Robert DeNiro from Casino. The second one from the right shows Robert DeNiro and Ray Liotta from Goodfellas.
The mobsters

What to miss

Chicago Style Deep Dish Pizza

The Best of the Windy City - skip the deep dish pizza. Image of a Chicago Deep dish pizza on a wooden tray. A slice is being removed from it.

If you like waiting an hour to eat a slice of pizza soup, by all means have some. We get it. It’s “local” but really, it’s not great and it’s super heavy. And you’ll be walking back to your hotel room with 9 pounds of leftovers. But if you really feel the need to know for yourself, we recommend Giadornos.

Where to stay

In the City

Location, location, location – The Hilton on Michigan Ave.

You’ll feel ultra fancy in these swanky digs but the price actually isn’t all that bad. And you’re right on Michigan Avenue so you can walk almost anywhere.

The Best of the Windy City - stay at the Hilton on Michigan Ave. Image of an ornate lobby. The walls are made of marble and there is a golden statue in the middle.
Images courtesy of Hilton
Image of the front of the Hilton. It's a large brown building with golden lobby doors and the top floor is beige stone. There are four towers. On either end the towers are twice as large as the two towers in the middle and all the towers are connected.

Outside the City

The Graduate Hotel (FKA the Homestead) – Evanston, IL

Just 14 miles away from downtown, The Graduate is my favorite hotel. It’s close enough to get to any activity in the city fairly quickly but it’s away from the crowds. Evanston is wonderful and walkable town, full of coffee shops and book stores. The nightly room rate is reasonable and you’ll feel like you’re staying in an apartment rather than a hotel.

The Best of the Windy City - stay at the Graduate in Evanston. Image of a living room with a sofa, coffee table, recliner and a a writing desk.
Our living room
Image of a dining table and chairs adjacent to a small kitchenette. A full sized white refrigerator next to a beige counter top. White cabinets are above the fridge and below the counter.
Kitchen & dining
Image of bathroom. The walls are covered in a beige tile with a small band of black tiles midway up. There is a full size bath tub with a shower curtain, a pedestal sink and toilet. The floor is covered in light brown tile and a beige rug is in front of the tub.
Retro bath
Image of wooden door with the number 714 and a brass knocker on it.
Interior room door!!
Image of a large porch with 7 white columns and a sign that reads "Graduate Hotels".
Courtesy of the Graduate Hotel

Adult beverages anyone?

In the city

Headquarters Beercade

What can I say? This places lets you play vintage arcade games FOR FREE while you sip craft beer and wait for your hand tossed pizza to finish cooking. It’s like my 15 year old self, died and went to heaven.

A man and a woman smiling at the camera and holding two glasses of colorful beer
Craft brews at HQ
Woman playing pinball at row of pinball machines.
Wishful pinball wizard
A neon sign that reads "Don't Grow Up It's a Trap"
Truer words…

Just outside the wind

Bat 17 – Evanston, IL

A great place to dash away from the busy city and grab a craft brew and a hearty sandwich. And during October, they REALLY embrace the “bat”!

The Best of the Windy City - have a drink or two at Bat 17 in Evanston. Image of a witch holding a banner that reads "Beware! Enter at your own risk!" It is written in what looks like blood.
Image of the bar with many taps. Colorful posters line the walls. There are several wooden tables and chairs in the main area with customers eating and drinking.
Image courtesy of Leeks Lim

Stuff to do (other than run the Marathon)

Adults only

Sing your heart out at Howl at the Moon

This is our FAVORITE thing to do when in the city. If you love music, or even like it, you’ll have a good time. The cover charge is only $5 on weekdays and $10 on weekends.

The Best of the Windy City - sing your heart out at Howl at the Moon. Image of a band playing on a stage. There is a person seated on a piano bench, playing and singing into a microphone. There is a woman to the front of the stage playing a bass guitar. There is a man seated on the piano playing the guitar. Another man is seated on something above the piano and is playing a bucket like a drum. A man on the far right is standing on the stage and singing into a handheld microphone.

With the Fam

The Lincoln Park Zoo

Not only will this little zoo allow you to get up close and personal with some wild beasts, it’s FREE!!

The Best of the Windy City - visit the Lincoln Park Zoo, Image of the Lincoln Park Zoo sign. It is made from stone blocks and replicas of animals in bronze are at the top.
Image of a rhino smelling the ground.
Image of a flock of flamingos by the water. The one closest to the camera is stretching his wings.
Image of a male lion behind fencing in front of a painting of the savannah. A log is directly behind him.
ACTUAL LIVE LION – not a display lion!

We hope you enjoy your time in the Windy City. Remember, if you have questions about traveling to the city, please feel free to reach out to us. And if you’d like to be the first to hear about any of our new recommendations, consider subscribing for free today!

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