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Jamie’s Destination “Do”s and “Don’t”s: Chicago

Jamie at The Bean

Welcome Back to our Friday Blog Series: Jamie’s Destination “Do”s and “Don’t”s, where our favorite Travel Planning Aficionado shares her wealth of knowledge and experiences about traveling the world! After every trip to a new destination, Jamie gives us her perspective as both a traveler, and a travel advisor, through a quick but comprehensive list of what to do or not do at each vacation location!

As many of you who follow along know, Jamie just got back from a part business trip/part family vacation to Chicago! Exploring a city makes for a fantastic long weekend getaway, especially if you have to travel for work and can bring the family along and extend the trip a few extra days. Cities across the country (and the world) each have their own personalities, with tons to do, see and learn around every corner. Jamie and her girls really took advantage of so much that Chicago has to offer on their start of summer trip!

So Let’s Go Explore Chicago! But First…

Chicago River

Jamie’s “Do”s and “Don’t”s for Chicago!

Top Favorites, and Jamie’s “Must Do” Experiences

Room View from Chicago Four Seasons

1. DO Stay on Michigan Avenue

Known as The Magnificent Mile, Michigan Avenue is the hands down the heart of the city. Between the high-end shopping, the Art Institute of Chicago, the Chicago Water Tower, and a plethora of fabulous hotels and restaurants to choose from, you could easily spend a weekend exploring just this street (though you shouldn’t of course, since we still have a whole list to get through!). Jamie’s personal favorite place to stay in Chicago is the Four Seasons on Michigan Avenue, because of its amazing views of Lake Michigan. 

Boat Tour

2. DO Take an Architecture Boat Tour

Chicago is definitely an architectural delight for design aficionados, and also anyone who just enjoys and appreciates interesting design! One of the best ways to take in all the unique and fascinating buildings throughout the city is by taking a boat tour! With the extra bit of distance that being on the water allows, you are better able to see what makes the Chicago skyline so beautiful. Jamie particularly loves this Chicago Lake and River Architecture Tour, and highly recommends it to anyone who visits Chicago! Pro Tip: Be sure to ADD ON the Lake portion of the tour; you don’t want to miss going through the boat lock from the Chicago River to Lake Michigan.

Lou Malnati's

3. DO Go for the Deep Dish

As always, one of the best parts of traveling, whether it’s to somewhere new or familiar, is indulging in all the local culinary delights! And Chicago is super well known for its famous Deep Dish Pizza! There are an abundance of great pizza places to try throughout the city, and Jamie and her girls definitely tried a fair few, but they all agreed that their favorite was Lou Malnati’s. Besides the traditional options, Lou’s also offers gluten-free options, too, which is a really big deal for Deep Dish Pizza, because the defining characteristic is the crust, and to get it right in a gluten-free version is no small feat!

Jeni's Splendid Ice Creams

4. DO Save Room for Ice Cream

Is there a more winning combination than great pizza for dinner and ice cream for dessert? If there is, I haven’t found one! And like pizza options, there are tons of great places to get ice cream in Chicago, but Jamie and her girls also agree that you’ll get the best ice cream from Jeni’s Splendid Ice Creams, and though there are many locations throughout the city, they particularly loved the Jeni’s in Connors Park for its adorable atmosphere!

Top Tips that Jamie Learned Along the Way

Chilly Boat Ride

1. Check the Weather

Chicago is one of those places where weather is always a wild card. It can be chilly in the summer, or you can get a random 60 degree afternoon in January somehow. With the winds whipping off the lake and bringing rapid changes and sometimes unexpected weather, it’s always a good idea to keep an eye on the weather in the weeks and days leading up to your trip, so you know what to pack and what to expect weather-wise. And even then, it’s still a good idea to pack an extra layer, just in case!

Chicago Architecture

2. Take a Hop-On/Hop-Off Bus Tour

Many larger cities have some version of the Hop-On/Hop-Off Bus Tour, and the Big Bus Tour in Chicago is the best way to start your exploration of the city! In fact, no matter what city you’re in, if there is a Hop-On/Hop-Off tour, it’s a great option for your first day because it gives you an overview of many of the major landmarks and attractions throughout the city, with the opportunity to “Hop Off” and explore more wherever you want, thereby setting your own pace, and getting to take a closer look at what you’re most interested in. Jamie recommends this  Hop-On/Hop-Off Big Bus Tour while you’re in Chicago. 


3. Visit Navy Pier

While many places boast a quintessential carnival pier, Chicago’s Navy Pier is undoubtedly one of the best. Navy Pier is just as rich with history, museums and the arts as it is packed with classic carnival fun. You’ll find seasonal events throughout the year, including fireworks, boat tours and cruises, and live music and theatre to grab your attention. Of course, you should plan to take a ride on Centennial Wheel, with spectacular views of the skyline, and history dating back to the 1893 World’s Fair. And don’t forget to grab a famous ice cream from The Original Rainbow Cone!

Top “Must-Don’t”s, or Things Jamie Would Do Differently

City Park

1. DON’T Skip the Parks

While you may be tempted to think that all Parks are the same, so why bother spending your vacation time in a city park, DON’T Skip the Parks in Chicago! This was *almost* a mistake that Jamie made, but thankfully, she was persuaded by her daughters to check out Maggie Daley Park, and was SO glad she did! According to Jamie, “the design (of the park) is simply stunning, and the bridge connecting Maggie Daley Park to Millenium Park, designed by Frank Gehry, is more fantastic than I can describe! So don’t be me (a naysayer), and make sure you just go to the Parks!” Also, while you’re there, grab a famous Chicago Hot Dog near the skating rink, and enjoy the scenery while you eat!

Chicago Beach

2. DON’T Miss the Beaches

Yup, that’s right, beaches; Chicago has over two dozen great beaches thanks to its location on the shore of Lake Michigan. And whether your preferred beach activity is boating, kayaking, paddle boarding, jet skiing, volleyball, swimming, or just relaxing with a great book or delicious drink, you’ll find all of it within the 26 miles of Chicago’s lakefront coastline, including an 18 mile Lakefront Trail. Of course, most of the beach activities are seasonal for summer, but don’t underestimate the beauty of beaches in winter, too (just bundle up, because Chicago is called the Windy City for a reason!).

Jamie and The Bean

3. DON’T Forget to Take a Picture with “The Bean”

Yes, it’s touristy, and yes, you’ll laugh at your fun-house-mirror-like reflection, but taking your picture with “The Bean” or, as it’s known officially, Cloud Gate, is basically required to prove you actually went to Chicago. And, while you’re in Millenium Park, don’t miss the rest of the fabulous art and architecture on display, including the Jay Pritzker Pavilion, the Crown Fountain, and Lurie Garden. 

And…that’s a wrap of Jamie’s Destination “Do”s and “Don’t”s for Chicago!

Chicago at Night

Ready to Plan?

Now that you have all of Jamie’s best advice for getting the most from your city exploration of Chicago, are you ready to plan your own metropolitan Adventure? Contact your favorite Love of the Magic Vacations Travel Advisor or email to start planning today!

Just like last year, in 2023, a new Destination “Do”s and “Don’t”s list will come out the Friday after Jamie returns from her latest trip! And you can find links to all of Jamie’s 2022 Travel Tips at this Blog: Jamie’s 2022 Destination “Do”s and “Don’t”s: A Recap

Jamie and Girls in Chicago

Looking for more of Jamie’s Destination “Do”s and “Don’t”s?

So far, we have: 

Jamie’s Destination “Do”s and “Don’t”s: Group Cruising

Jamie’s Destination “Do”s and “Don’t”s: Universal Studios Orlando

Jamie’s Destination “Do”s and “Don’t”s: River Cruising

Jamie’s Destination “Do”s and “Don’t”s: Disneyland

And don’t forget to check out our Inspiring Itineraries as well, featuring a Perfect Plan for your next vacation, and highlighting a new destination each month! You can find links to all of 2022’s Inspiring Itineraries in this Blog: A Year of Inspired Travel: 2022’s Inspiring Itineraries, Month by Month

Dos and Don'ts Chicago





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