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Top 10 Things To Do In Chicago With Out of Town Guests

Top 10 Things To Do In Chicago With Out of Town Guests
Top 10 Things To Do In Chicago With Out of Town Guests

Chicago is such an amazing city! There’s so much that you can see and do, so when friends and family come to visit, it can be a little overwhelming to pick and choose. Well, if you’re wondering what to do in Chicago when you have out of town guests, here’s my fool-proof list of the Top 10 Things To Do in Chicago!

Top 10 Things To Do in Chicago With Out of Town Guests

1. Welcome Out of Town Guests with a Chicago-themed gift bag

Send Them Chicago gift basket called "Windy City Welcome"

There’s so much to love about Chicago, and it’s hard to squeeze it into one trip, so when I have out of town guests visiting Chicago, one of my favorite things to do is to welcome them with a gift basket filled with Chicago-themed treats. Send Them Chicago has some great gift bags that you can order and customize as needed. My favorite version is called “Windy City Welcome,” and it comes with a Chicago Flag Mug, a sampler tin of Garrett’s Popcorn, a pop-out fold up map of Chicago, classic Frango Mint Chocolates and sample of some melt-in-your-mouth Chicago Butter Cookies.

Send Them Chicago is a locally-owned and operated business and works with other independent artisans and Chicago-based businesses to put together a sampling of Chicago treats, which are wrapped up in a bow and ready for your guests. Nothing says “Welcome to Chicago” like a gift basket full of treats!

Read more about Send Them Chicago gift baskets here >>

2. Take a Dinner Cruise on the Odyssey at Navy Pier

Dinner Cruise Chicago Odyssey

One of my all-time favorite things to do when I’m hosting out of town guests is to book tickets for a Dinner Cruise on the Odyssey – especially if it’s a special occasion like a birthday or anniversary trip! The Odyssey docks at Navy Pier and heads out into Lake Michigan for a 2-3 hour tour – complete with dinner and dancing!

From the windows and the upper decks of the Odyssey, you have the most unbelievable views of the Chicago skyline – both at sunset and at night. The view alone is worth the trip, but the beautiful setting, excellence service, delicious food and a rockin’ dance floor are all welcome bonuses. It will be an unforgettable experience for you and your guests!

See more from my latest experience on the Odyssey >>

3. Visit the John Hancock Building and get the 360 Chicago Experience (don’t forget the TILT!)

View from 360 Chicago Observation Deck

I grew up visiting Chicago and going to the Sears Tower (now Willis Tower), and while I loved the experience, I do remember it taking forever to get through the line and finally make it to the top. Now that I live in Chicago and have out of town guests – I tell them to skip the Willis Tower and head straight to the 360 Chicago Observation Deck on the 94th floor of the John Hancock building.

The 360 Chicago view CANNOT be beat and it’s so convenient to get to (it’s right on Michigan Ave). Fewer crowds means a more pleasant, laid back experience. And the Tilt attraction is SO cool — it’s an enclosed glass platform that extends away from the building at a 30 degree angle. It’s amazing, and I swear NOT as scary as it looks! So be sure to buy tickets for that too!

Read more about my 360 Chicago experience with my family here >>

4. Shop Local Boutiques (Get off Michigan Avenue and visit some neighborhoods!)

The Magnificent Mile is undoubtedly a shopper’s paradise, but truthfully – there aren’t many stores there that you can’t find in every other city in America. One of the best things about Chicago is that it’s a city of distinctive neighborhoods – each one has its own personality and tons of independent shops and boutiques that offer unique, unusual and fantastic finds. I always beg my out of town guests to get off of Michigan Avenue and shop local boutiques.

Some of my favorites are the Trendy Sparrow and Bossbabes Pop Up Shop located in the Block 37 building on State Street and the M2 Boutique located in Wrigleyville/Lakeview.

Read about a few of my favorite local Chicago boutiques here >>

5. Score Last Minute Tickets to Plays (like Hamilton!)

Hamilton Tickets Chicago

Seriously, this one took me by complete surprise. The last time my family visited, my mother and sisters saw a sign for Hamilton on the top of a cab and decided to drop by the Private Bank Theater box office to see if there were any tickets available. AND OMG, there were!!!

As a Chicago local, I’d been trying to get tickets to Hamilton for months, but they’ve been sold out for ages. And my family literally just waltzes into the box office and asks for 5 tickets for that night’s show, and we scored 4th row seats for a ridiculously reasonable price. I was SHOCKED. But apparently, that’s the secret to scoring tickets to major theater shows – show up in person at the box office when they open (like at 10am) and scoop up some day-of tickets.

Read more about our last minute Hamilton score here >>

6. Visit a Chicago Museum (MCA or Art Institute)

Chicago Museums, MCA, Art Institute

We have some of the best museums in the world right here in Chicago, so it is a mistake not to make room on your agenda to visit at least one when you’re in town. They are a bit of a time commitment though – easily taking half of your day or more. However, there are two museums that are right downtown that are easy to get to and offer the most “bang for your buck.” The two museums you should visit when you’re in Chicago are: the Museum of Contemporary Art and the Art Institute of Chicago.

7. EAT. Eat some more. And then Top it Off with Dessert.

Chicago Food, deep dish pizza, steak, hot dog

Chicago is a city that knows how to EAT. We have an incredible food scene here, and there’s something delicious for every palette and every budget! If you’re looking for the best Chicago Deep Dish pizza, head to Giordano’s. Want an incredible steak? Head to Gibson’s Steak House. For a meal with an unparalleled view, make reservations at the Signature Room at the John Hancock Building. Looking for Chicago Hot Dogs? Head to Superdawg Drive In on the northside. Best locally brewed beer? Half Acre is your answer. Chicago Distilling Company in Logan Square has the best Gin I’ve ever tasted – Finn’s Gin. Ice cream? Look no further than Margie’s Candies in Wicker Park. There are so many options and so little time, so just do your best to make it to a few of those places!

8. Go to a Cubs or Sox Game

Wrigley Field Chicago, Cubs Game

Cubs or Sox? Chicago is one of the few cities in the U.S. that has two major league baseball teams – and we love them both! Locals might declare allegiance, but if you’re visiting, you can’t go wrong with attending a baseball game at either park. Choose Wrigley Field for the ambiance and the history. Choose Guaranteed Rate Field (formerly Cellular Field) for a newer, more state-of-the-art baseball experience.

9. Visit Cloud Gate, a.k.a “The Bean”

Cloud Gate, The Bean, Chicago Sculpture

This is one of those things that every tourist must do — and even the locals think it is cool. Officially called Cloud Gate, locals have nicknamed it “The Bean” since its shape resembles a coffee bean. Whatever you call it — it’s just downright cool.

Located in the heart of Millennium Park, the bean is a super reflective stainless steel sculpture that reflects the Chicago skyline and the clouds in the sky — and you if you’re visiting. The sculpture arches in the middle and you can walk underneath it and look up into a seemingly endless reflection of yourself. It’s seriously cool and is a totally instagrammable moment!

10. See a Comedy Show

Second City Logo

Without the Chicago improv comedy scene, there would be NO Saturday Night Live. Chicago basically invented this style of comedy and has been an incubator for some of the best sketch comics in the world. There is not a single night of the week that there’s not a comedy show in Chicago. My favorites are (of course) Second City and iO for the more traditional improv format. Baby Wants Candy is a fun, fully improvised musical, and Cupid Has A Heart On is great for those who like things a little raunchier.

If you manage to do one or a few of the things on this list of Top 10 Things To Do in Chicago With Your Out Of Town Guests, then they are sure to have an amazing time. You’ll go down in history as the best host ever!

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