Chicago has so much to offer- tons of food choices (Hello pizza!), festivals, shopping, art museums and more! However, all those options can feel stressful if you have limited time. My partner and I are taking a quick, 4-day getaway to Chicago (we are leaving from southern Minnesota on a Friday and returning Monday) and we have put a lot of planning into our “mom and dad” trip to make the best use of our time. We want to share with you our favorite experiences from Chicago in hopes you can add these stops to your itinerary!

Disclaimer: All posts are written from my experiences and my opinions. There may also be some affiliate links, meaning I may make a small commission if you make a purchase at the website. All of my affiliates I genuinely love and have used the products long before affiliation.

Shop Backcountry’s Massive Selection of Gear, Clothing, and Outerwear on Sale!

What’s the Best Time of Year to Visit Chicago?

Chicago is a fun place to visit any time of the year. Once again, it all comes down to what your interests are and what you are hoping to do while you are in Chicago. We usually visit early summer because we enjoy the music festivals at the park and the water activities. Walking all over the Millennium Park area was one of my favorite things to do, and I am not the biggest fan of cold weather- so we come here during summer time to do this. (I would like to note that being in Chicago during Memorial Weekend was an interesting experience. Some of the locals mentioned it’s one of the most dangerous times of year to visit Chicago. We also heard on the news that they tripled police force during Memorial Weekend- which we could tell they did).

Where Did We Stay?

Hotel Julian (right across the Nutella Cafe).

When you are in Chicago, it can be easier and quicker to walk place to place instead of driving. Navigating the traffic, thick, endless floods of pedestrians and paying steep fees for parking are all reasons you should make sure your lodging location is right where you need it to be. For us, we were attending a music festival, Suenos, located in Grant Park. We also knew we wanted to visit Millennium Park, Sky Deck, the Chicago Riverwalk and Lake Michigan as well. Using, we were able to book a hotel that was located in the middle of it all-and then some!

We chose to stay at Hotel Julian, which was a block away from Millennium Park and only a few blocks away from the Chicago Loop. Hotel Julian is a very artistic, beautiful hotel with art and books everywhere. They have various amenities including a fitness gym and house the restaurant, About Last Knife, on the first floor. I will say it’s important to scope out your parking areas. Also take note that there are many public parking garages that are closed all weekend. So, if you park your car there Friday, you cannot access it until Monday. The closest parking garage we found to the hotel that stayed open all weekend was the Grant Park South Parking Garage.

There are many shopping options nearby like Ross, Macy’s, Francesca’s, Chanel, Target, Walgreens, Urban Outfitters, Dior and Sephora- just to name a few. Right next to Hotel Julian for food is Starbucks, Smoothie King and a second Starbucks (right out the back door of Hotel Julian), Nutella Café (the only one left in the world- but more on that later!), Bubblicious Boba tea, Sweetwater Tavern and Grill, The Billy Goat, Dunkin Donuts, Emerald Loop Bar & Grill, Popeye’s, Wild Berry’s Pancakes & Café, Rosebud Randolph’s (Italian), Giordano’s Pizza, The Walnut Room, Russian Tea Time, The Gage, Hot Woks’s Cool Sushi, Remington’s and Tavern on the Row. Again, these are only a few of them! Neat activities within walking distance are Chicago Cultural Center, Millennium Park, Chicago Riverwalk, Lake Michigan walk way, Columbia Yacht club, Design Museum of Chicago, Sky Deck, Fountain of the Great Lakes, South Garden, The Art Institute of Chicago, Grant Park, Maggie Daley Park, The Museum of Illusion Chicago, The Chicago Theater and many more!

So many books everywhere at Hotel Julian (peep the background!).

Overall, we loved our stay. The view was fantastic- we were so lucky to be able to see so much of that area from aerial view and would definitely come here again because of how gorgeous our view and room was. We also had the perfect location and great service.

If you would like to check out Hotel Julian, click here!

While I enjoy Airbnbs home rentals, when I go to Chicago I usually go the hotel route (you can still book hotel rooms through Airbnb! And it’s pretty smooth going!). Other hotel options in this area are Hampton Inn Downtown/The Loop Chicago, Fairmont Chicago Millennium Park, Millennium Knickerbocker Hotel Chicago, Swissotel Chicago, Stay Pineapple- The Loop Chicago, Cambria Hotel Chicago Loop, Fairfield Inn & Suites Downtown Chicago, Londonhouse Chicago Curio Collection by Hilton, St. Jane, Hyatt Regency Chicago and many others!

How Do You Get There?

Being we are from Minnesota, going to Chicago is usually a 5 hour drive (depending on traffic), so we just do a road trip instead of booking a flight & it’s a pretty easy drive. We always try to be mindful when we travel and time our arrivals in cities before or after the rush hours like to and from work. I-90 makes up most of our drives and it would be similar for anyone traveling from MN, WI, SD, ND, etc. If you are coming from out of state and want to fly to Chicago, you can book a flight to O’Hare International Airport (click to book your flight!).


Stops are not listed in any particular order.


Can you really justify visiting Chicago without trying a slice of the Chicago famous, deep dish pizza? We definitely couldn’t! We were honestly so excited about this and made it one of our first stops in Chicago. We liked the reviews we read about Giordano’s and decided to try them out. They did not disappoint! The only thing we wished we did differently was order a smaller size. The Chicago style pizzas are so deep, that even if you have the smaller size, it’s A LOT of food because of how thick the pizza slices are. Also, if you are ordering pizza for delivery, it’s not a bad idea to order hours ahead of time. The wait time can be extreme!

Check out Giordano’s here!


Photo Credit Bubblelicious Facebook

If you are a Boba tea fan, this selection is for you! I tried the Tiger Sugar Boba Milk tea and it was phenomenal. They have an extensive menu and for us was conveniently located right across from our hotel and down the street from Millennium Park.

Check out Bubblelicious here!.


A trip to Millennium Park is not complete without a selfie with Cloud Gate aka The Bean- one of Chicago’s major landmarks! I was very motivated to explore some of the beautiful sites of Chicago so I actually got up at 530 am to explore some of Millennium Park area. This went perfectly considering most shops do not open until 10 am. There was probably a handful of people around the park- that’s it! Fast forward to around 11 am- the park becomes very thick with visitors. My favorite part about “The Bean” is how it reflects the city’s skyline. It truly is a wonder & I am grateful I was able to walk around and under it!


I honestly was not even expecting to stumble across the Lurie Garden, much less fall in love with it! There was something magical about a beautiful garden in them middle of a city surrounded by sky scrapers. I spent a good amount of time here exploring the different types of flowers, journaling and taking in the view. Flowers they feature change with the seasons. You can read more about the flower collection and this wonderful secret garden here.


The Millennium Monument at Wrigley Square was actually my first stop at Millennium Park. The columns are made out of Indiana limestone, and you can find the names of the 122 Millennium Park founders carved at the base. I found this spot a nice place to relax before venturing towards busier areas due to it’s close proximity to Michigan Ave and Chicago Cultural mile.

Explore Wrigley Square and the Millennium Monument here.


As you can tell from the map, Maggie C. Daley park is filled with neat sights to see and family activities. It is home to a massive rock climbing wall, a mini golf area, beautiful picnic groves, fun play ground, the cancer survivors’ garden, ice skating ribbon (in the winter), tennis courts and roller blading, micro scooters and bungee jumping for the entire family. I loved the layout and architecture of this park-it’s so huge in person! Our trip was just the two of us, but we made note of stopping here to enjoy activities if we visit with our kids next time.

Explore Maggie C. Daley park activities here!


The Jay Priztker Pavilion is an out door amphitheater with a central location in Millennium Park. It can technically host a show for 11,000 people. The set up is stunning. I was able to explore the area since I got to the park very early. They were working on sound checks for the upcoming performances that weekend. While our show was at Grant Park, it was neat to sit out on the grass facing the stage and take in yet another one of the beautiful architectures in Chicago.

Plan your visit to Chicago’s Jay Pritzker Pavilion performances here!


If you love my shades, check out the website by clicking this image & get $20 off. They have everything from blue light glasses to every shape and shade you can think of!

My favorite part of Chicago was exploring the Sky Deck and The Ledge located in Wills Tower. While there are two parts to this experience, it makes the most sense to have both under the same entry. First of all, let’s talk about planning your visit. I HIGHLY encourage you to buy your ticket days in advance and book for the earliest time you can. We booked our ticket for 8:30 am. Otherwise, the line can be obnoxious and the Sky Deck can get crowded (they get over 1.7 million visitors per year!). There is also the option to buy a fast pass to be in a shorter line (of course, it’s more expensive).

We enjoyed going earlier because we were not as rushed to enjoy reading and exploring the exhibits prior to entering the Sky Deck. You will also be in an elevator going to and from the Sky Deck with A LOT of people packed in. With COVID-19 still raging on, it’s not a bad idea to bring a mask and hand sanitize with.

Also note that Willis Tower itself offers extensive shopping and dining experiences- you could honestly spend your entire day here!

The Sky Deck experience starts off with an interactive exhibit of the history of Chicago with a focus on the city’s unique architecture. There is even an exhibit where you can walk down a subway cart where the outside moves and gives you glimpses of past events. Its pretty amazing! Afterwards, you will go through the selfie exhibit, allowing you to take pictures with some of Chicago’s most famous landmarks all in one place! We had a lot of fun with this.

After the selfie exhibits, we got in line and took the elevator all the way to the top- which is 1,353 feet above the ground! Willis Tower’s Sky Deck is the highest public viewing area in the United States and the second tallest building as well. It is the 12th tallest building in the world. The elevator felt like it was swaying a little bit when we got to the top (but we were safe!). The Sky Deck is INCREDIBLE. I can’t say enough how this needs to be on the bucket list! We were blessed with clear weather, so we were able to see over so much of Chicago. You literally get a 360 view.

There is a separate area were The Ledges area. We got in line (which moved quickly) and there was an attendance present that took a picture for us, then we were able to take our own pictures. I was so excited to get on the Ledge, but once I was out there, I realized how scary, yet beautiful it is! I wasn’t one of the brave people doing a head stand on the Ledge, but I stayed for a photo op!

Examples of images available for purchase that Sky Deck takes for you.

There are souvenirs available for purchase when you are at the Sky Deck. You can also purchase the pictures they take for you. we got these 4 images and 2 large ones (hanging up in my house now) for $42. I usually don’t purchase these things, but decided to today because we had such a great time.

To plan your trip to Willis Towers’ the Sky Deck and the Ledge, visit their website here. You can also go online to see live video footage from the Sky Deck, check out other neat facts and print out fun activities for kids.


If you like EXQUISITE donuts and coffee to kick your day off, consider visiting Stan’s Donuts and Coffee. They have a great selection of donuts that I have not seen anywhere else. They also have vegan options (which are the ones I tried) and they do not disappoint. I bought the pistachio glazed donut for my partner, which he gave epic reviews on. They also offer breakfast sandwiches and burritos. This was a convenient place for us because it was right across Hotel Julian.

Take a closer look at Stan’s Donuts & Coffee menu here.


Michigan Ave (and the surrounding areas) gives you access to a variety of stores-if you are a shopper, you will be in heaven! I am a big Francesca and Urban Outfitters fan, so those were my stops. If you are into celebrity-style name brands, you can also go into Gucci, Burberry, Chanel, Dior. For more bargain shoppers, there is a 2-story Ross we checked out as well (similar to TJ Maxx). For kids, they have Smile Kids, Kido and Wish Kids, Osh Kosh B’gosh, Carters to name a few.

If you are wanting to go shopping in Chicago, click here to see the street shopping guide. If you are interested in shopping along the Magnificent Mile, click here!


Are you familiar with Lollapalooza, Summer Smash, Freaky Deaky , Chicago’s Blues Festival and many others? Grant Park is one of the common venues to host some of these, with an amazing location in a park nestled within the skyscrapers. We attended Suenos, a Spanish festival in it’s first year. I really enjoyed it’s location at Grant Park. We were able to try a variety of food trucks and really appreciate the view of the city along with great music.

Are you looking for festivals to attend in Chicago? Click here to view upcoming events.


Our view of Navy Pier

I went for a morning stroll along Lake Michigan’s Lakefront Trail. This trail is an 18 mile paved trail in eastern Chicago that follows along the Lake Michigan shore. Along the trail are scooters you can rent to ride the trail over by the Navy Pier or to the entrance of the Chicago Riverwalk. I enjoyed seeing the yachts and boats in this area. I was so surprised at how blue Lake Michigan is- the stroll is worth the view!


It definitely is not St. Patrick’s Day anymore because the Chicago River definitely does not look green! There is simply so much you can do along the Chicago Riverwalk. There are areas you can stop to eat, have a drink, sign up to go on a cruise, have your kids play on the unique play area, sign up for kayak lessons, shop or float down the river in a Tiki bar- the choice is yours!


Unfortunately, Crown Fountain did not have the water running the couple time we visited it. Crown fountain is a public art and video sculpture in the Chicago Loop area. We had a perfect view of this from our room, and could actually make out all the faces they were playing on the screen. I had to post a couple of them for fun! We would definitely go back to the area to see if the water is running.


Two Zero Three Café was delicious and around the corner from Hotel Julian. I have this rule that when I travel, I try new places. We had 2 Starbucks and a Dunkin’ Donuts right by us, but we were determined to try something more local to Chicago. Two Zero Three is a downtown café and wine bar. To go inside, you must enter through Virgin Hotels. They serve La Colombe roasts featuring their exclusive drinks Queen Bee (Espresso, vanilla, honey, oat milk), Mocha & Chill (Espresso, cinnamon, chocolate, almond milk) and Starr Bocks (Espresso, caramel, vanilla, 2% milk). I tried the Queen Bee with a Spinach & Artichoke filled-pastry- and I absolutely would get it again!

For more information on Two Zero Three, click here.


The cherry on top of our trip was the Nutella Café- apparently the only one left in the country because the store in New York closed during COVID-19. The line for this place gets VERY long. I observed this a couple days before we went. On our final morning in Chicago, I actually got in line 40 minutes before the store opened. About 10 minutes after I got in line, 8 more people also lined up for some Nutella- it was crazy! But if you are a Nutella lover, you will enjoy their creativity with Nutella. My favorite Nutella item I tried was their Panzanella, featuring yogurt, fresh berries, pound cake, and Nutella-a must try for if you visit!

Check out more about the Nutella Café here!


The Art Institute of Chicago

As you can imagine, there will always be thousands of fun things to do, explore and experience in Chicago. We already have a few things we are hoping to do on our next trip and wanted to share them here with you!

  • TASTE OF CHICAGO: We just missed this event by a couple of weeks! Taste of Chicago Festival showcases the variety of different foods in Chicago hosted by local food places. It’s the best way to get a taste of Chicago in one spot (accompanied by great music of course!). The food vendors accept cash and credit card and admission is free into the festival. Here are the dates for 2022 and you can also click here for more information:

Saturdays, June 11, 12-8pm • Taste of Chicago Austin

Saturday, June 18, 12-8pm • Taste of Chicago Pullman

Saturday, June 25, 12-8pm • Taste of Chicago Little Village

Friday–Sunday, July 8–10, 11am-9pm • a bite-sized Taste of Chicago Grant Park

  • THE ART INSTITUTE OF CHICAGO: Art from all around the globe and during different time eras is featured at the Art Institute of Chicago. There are virtual events as well, but nothing beats seeing this exhibits up close in person. Click here to plan your visit.
  • THE MUSEUM OF ILLUSIONS: A fun family activity we have been wanting to do is the Museum of Illusions, which is an interactive museum of, well, illusions! Being we did not have our kids with us during our trip this is something that has moved back to a future trip- but it’s on my bucket list for sure! Click here to view and plan your visit!
  • CHICAGO CITY CRUISES ON- NAVY PIER: I have always wanted to go on a cruise in Chicago to see the shoreline and also because there are so many cruises to choose from. Click here to plan your cruise.
  • WILDBERRY PANCAKES AND CAFE: Okay, hear me out on this one. Go to their website and view the menu. Tell me your mouth isn’t watering- because mine sure is! Click here to see the menu.
  • TILT THRILL RIDE: It was between The Ledge and the Tilt Thrill Ride for us, but we chose The Ledge. The Tilt looks VERY intense if you are scared of heights (which I am- a little bit!). It’s still something we want to make sure to try during our next visit to Chicago! Click here to grab your tickets.

Ready to pack your bags and experience Chicago? Share in the comments which stop you are most excited about and what part of Chicago you will be traveling to!

Looking for more travel tips? Make sure to check out and pin these post.

Follow Along our Family Travels here:

Looking for other Outdoorsy Experiences? Check out these options!


  • Romantic Getaway in Minnesota : An Itinerary for a Weekend Getaway Lakeside in Harris and Chisago Lakes Area

    Romantic Getaway in Minnesota : An Itinerary for a Weekend Getaway Lakeside in Harris and Chisago Lakes Area

    I will admit- I have driven through the Chisago Chain of Lakes area (about 30-50 minutes north of Minneapolis) on my way to Duluth or the North Shore. I never thought twice about visiting this unique area. What a big mistake I was making! Over the past couple of years, I have explored towns I…

  • 10 Ways to Enjoy USA’s Wine Country Napa Valley and Sonoma Valley

    10 Ways to Enjoy USA’s Wine Country Napa Valley and Sonoma Valley

    Wine country has been on my places to go for quite some time- save this list of highlights to experience when you travel Sonoma and Napa Valley! We decided to travel the Sonoma and Napa Valley region during our California coast road trip last summer. Both regions are located less than 60 miles northeast of…

  • 10 Fun Things to Do in Bayfield, WI

    10 Fun Things to Do in Bayfield, WI

    If you love Lake Superior, you will love Bayfield, Wisconsin. Bayfield is a fun stop if you are going on a road trip to the Upper Peninsula of Michigan as well. Located on the most northern tip of Wisconsin, this tiny lake town is the gateway to the iconic Apostle Islands. There are 21 islands…

  • 10 Favorite Things to Do in Lanesboro, MN

    10 Favorite Things to Do in Lanesboro, MN

    One hundred twenty miles southeast from the Twin Cities in Minnesota is the crown jewel of the great river bluffs region in Minnesota: Lanesboro! Lanesboro is a small town with a big reputation for it’s trail system, river activities (Root River) and gorgeous views of the rolling bluffs (especially stunning in the fall time!). My…

Comments +

Leave a Reply

Your email address will not be published. Required fields are marked *

Almost there!

Free guide

Feel empowered to take charge of your crossing off dream desintations from your bucket list!

Travel Love

Follow US

Hey there

Follow along on our social media platforms! We want to hear your travel and blog suggestions, questions and hear about inspiration of your own!
Instagram: @thetravelingwildflowerr