Best Weekend Getaway Itinerary: Chicago, Illinois (free mini itini!)

Ahh, Chicago. The Windy City. Chitown. The Second City.

Whatever you want to call it, it's a must-see. Between the nightlife, the art, the food, the history, the shopping, and the entertainment, you're guaranteed to have an epic weekend.

I've put together a "mini-itini", which is basically just a downsized itinerary (2 days instead of 7-10 days). Mini-itinis are great for getting a feel for what the city has to offer, what you might find yourself doing or eating while you're there, and if you could see yourself spending a few days there.

Note: If you'd like a personalized mini-itini (or full size itinerary) contact me at or through the Contact Me page. I offer personalized minis for $10 and full size for $20.

So, let's get into it.

Chicago Skyline

Chicago, Illinois: Mini-Itini Example

Day 1

9 am - arrive in Chicago

930-10 am - find parking and settle into hotel

1030 am - Millennium Park (Public park located at 201 E Randolph St.) This is where you'll find Crown Fountain, The Bean, wall climbing, and so much more.

12 pm - lunch at Millennium Park

1 pm - Visit Navy Pier (Located at 600 E Grand Ave.) This is where you'll find shops, restaurants, and even rides - like the famous Navy Pier Ferris Wheel! Occasionally you'll be able to find free concerts, free firework shows, and even free art shows there. (Does everyone else like the word 'free' as much as I do?)

5 pm - Hit Ed Debevic's for dinner (Located at 640 N Wells St.) Ed Debevic's is a 50's style dinner with a twist. The staff is supposed to be sassy to you. If you're familiar with Dicks Last Resort, this is a similar place. For those of you that aren't familiar, you might be wondering why anyone would sign up to have a fiesty server. Well, the food is great, and the servers are sassy, never rude. Plus, the staff has choreographed dances they break into while you're eating. It's one of the most entertaining places to eat.

*** If you don't have a sense of humor, it might be best to find another place to eat.

7 pm - Second City Chicago (Located at 1616 N Wells St.) Ever heard of Steve Carell? Stephen Colbert? Amy Sedaris? David Koechner? Tiny Fey? Know what they all have in common? They graduated from Second City, one of the most popular comedy schools in the US. Second City holds weekly sketch comedy and improv shows. You can buy tickets online or at the door, but I always suggest purchasing online because they sell out pretty quick.

9-10 pm - head back to your hotel (or to the local bar down the street)

Cloud Gate aka The Bean at Millennium Park

Day 2

9 am - breakfast at the hotel

10 am - Shopping on Magnificent Mile (Located at 625 N Michigan Ave). This is where you'll find all the best shops (Zara, TopShop, Chanel, Sephora, etc.) Make sure you bring quarters for parking meters and get ready to spend a few hours here. It's called Magnificent Mile for a reason, people.

12 pm - Lunch at Magnificent Mile

1 pm - Willis Tower/ Sky Deck (Located at 233 S Wacker Dr.) Formerly the Sears Tower, this is where you'll find the glass overhang above the city that you see every so often on Instagram. On the 103rd floor of the Willis Tower, the glass boxes extend almost 5 feet from the Skydeck. You can step out onto the boxes and it feels like you're floating above the city.

*** For those with a fear of heights, this might not be a great pitstop for you.

4 pm - Gangster and Ghosts tour (Departure point is located at 71 E Wacker Dr.) This is a 2 hour walking tour of Chicago with a historian. Your tour guide will tell you stories about the ghosts of Chicago while you walk by hotspots where world famous gangsters used to hangout.

6 pm - Dinner at Giordano's Pizza (Located at 730 N Rush St.) You can't leave Chicago without having pizza - it's just not right. If you ask around the Midwest, you'll hear lots of opinions about who has the best pizza in Chicago. But one place is sure to be mentioned more than once - Giordano's. And remember, while in Chicago, deep dish is the way to go.

8 pm - The Drifter (Located at 676-8 N Orleans St.) The Drifter is a Speakeasy (yes, really) hidden underneath the Green Door Tavern. It's exactly what you'd expect - drinks, live entertainment, and it's never too crowded.

*** Getting a reservation at The Drifter is highly recommended.

If you end up using this Mini-Itini, I'd love to hear how it went!