Chi-Town’s for the Girls (and Hockey)

Planning a trip to Chicago? As a Fora Travel advisor I can help and hopefully add in some perks too =)

In keeping with the “baby” theme this month (have you signed up for My Wealth Road’s newsletter?), I’m sharing details from a recent trip to Chicago for my Roads to Roam post. It wasn’t my first time being away from the kids, but it was my first time flying since Annie arrived over four years ago. I wasn’t a days drive or short boat ride away like prior girls’ trips, so I had some reservations about booking this one.

Long story short, my husband seemed uncertain about work and traveling for his close friend’s wedding. I could tell he felt bad about not going because the deadline to RSVP was approaching, and he hadn’t sent the card in. Joking (sort of), I suggested that I go with his sister while he stayed home with the kids. To my great surprise he agreed! If he couldn’t go, at least I’d be there to represent him. Rach and I would be the ones out on the dance floor all night anyway (the band was amazing btw)!

I went into planning mode. Checking which hotels still had room blocks and whether I had enough points to cover my flight on a holiday weekend. Last time I went to Chicago in February – for my cousin’s hockey game if you’re wondering ‘why on earth February‘. Believe it or not we still had a great time despite the frigid weather (I’ll share details from both trips). But I was excited to experience the warmer side of Chicago this time around. I was also excited for a weekend where I could eat at a restaurant and finish a glass of wine without fear of an epic toddler meltdown. I reveled in the idea of sleeping past 7 am and a couple days of only being responsible for myself. Sounds amazing right? And it was. But it took me days to let go of the ‘mom guilt’ I felt when it came down to actually booking the trip. What if something happened to me or the kids? What if the kids get mad at me for going? On a scale of 1-10 how selfish am I being?

With a little convincing from Rach (frequent texts of memes and pictures referencing anything girls weekend and Chicago), I was able to put aside my anxious feelings and focus on the excitement of the upcoming trip. And I’m glad I did. The wedding was absolutely beautiful. My kids had a great time with Dad (special trip to the toy store helped) and gave me the biggest hugs and smiles when I returned home. Thank God because I was now starting to worry they didn’t miss me at all!

Here are the highlights from my weekend trips to Chicago.

For this recent trip we stayed at the Hilton Chicago. Grant Park, Buckingham Fountain, The Art Institute of Chicago, Millennial Park and the Bean are within walking distance. Continue walking North and you’ll find entries to the Chicago River Walk and boat tours. Stop at the Sears (Willis Tower) on your ‘Loop’ back to the hotel.

Art Institute of Chicago

I visited the Art Institute during my February trip. It offers the perfect escape from the cold! Impressionism art is my favorite and the museum has a large collection of paintings from Monet and Renoir. There’s also a large collection of Andy Warhol’s iconic Pop Art. The museum is open daily from 10:30am – 5pm and Thursdays until 8pm.

Millennial Park & the Bean

One pro of going to Chicago in February was there were fewer crowds which makes trying to get that perfect picture of the famous Bean a little easier. Seeing Lake Michigan mostly frozen was certainly a sight to see. But warmer weather allows you to enjoy walking or biking through the park and along the trails on Lake Michigan. The park comes alive in the summer months when free events are hosted. The Jazz Festival was in full swing during our visit over Labor Day weekend. For maps, event and park information download the Millennial Park app.

Architecture Tour on the Chicago River

The Architecture Tour with Shoreline was my favorite part of touring Chicago. Our docent seamlessly mixed history and architectural design while sharing “the story of Chicago” as we cruised along the Chicago River. It was the best way to gaze at the skyscrapers and city skyline. We also scoped out restaurants to try along with Chicago River Walk. Tours are 75 minutes and run daily from Michigan Avenue or Navy Pier. Pick the location based on where you plan to explore before or after the tour. We took the 10:30 am tour from Michigan Avenue and walked along the river to have brunch at The Kitchen afterwards.

Sears (Willis) Tower Skydeck

For the brave and daring, the Skydeck at Sears (now called Willis) Tower allows you to walk out and view the city from a clear glass box. “The Ledge” is located on the 103rd floor! I don’t know if I was sweating from the drastic temperature changes (polar vortex outside, blasting heat inside) or a growing fear of heights. My sister had the nervous giggles in the elevator and wouldn’t even put her big toe on the glass. Somehow I convinced myself to walk out with my mom and aunts for a picture. I’m sitting because vertigo was kicking in. This was my experience, but it’s different for everyone. My mom and aunts were utterly fearless! The Skydeck is open morning and night 365 days a year. Check the website for opening/closing times during the month you travel.

The Tilt and 360 Observatory at the Hancock building

The great thing about the 360 Observatory is that you can enjoy stunning views of Lake Michigan and the Chicago skyline from the comfort of Bar 94 while your crazy family members hang 94 stories out of the building at the Tilt Experience. The signs assure you it can hold a four ton elephant, but I decided to pass on this one. I was afraid just watching people in line! Open until 11pm year round it’s an ideal place to watch the sunset and see the skyline light up at night.

Views of Lake Michigan from 360 Chicago

Cubs Game at Wrigley Field

We weren’t able to attend a Cubs game, but we did manage to meet up with Rachel’s childhood friend at Brickhouse Tavern directly outside the stadium. Yes, Stamford peeps – all roads eventually lead to the Brick. It was game day and the neighborhood was packed with fans at local bars and restaurants. I recommend attending a game if time permits and it’s not sold out. You can also tour the stadium and learn about its over 100 years of history.

View of Wrigley Field on game day from Brickhouse Tavern

Chicago Eats

I’m trying to remember the Italian restaurant we loved during my February trip. I’ll update this post if it ever comes to me. I always scope out restaurants to try before traveling. It’s the worst when your overpriced meal is mediocre at best. Shouldn’t all vacations revolve around your next bite to eat?

Harry Caray’s Italian Steakhouse in River North

Named after the beloved Chicago Cubs sportscaster, the restaurant serves “the finest USDA prime, aged steaks and Italian favorites”. The halls of this historic building are filled with sports memorabilia and possibly the ghost of Frank Nitti, Al Capone’s notorious enforcer. Click here to learn more about the history of the building dating back to the Prohibition era.

Keeping warm at Harry Caray’s Italian Steakhouse


I was skeptical about this place. I wasn’t overly impressed with Chicago deep dish pizza and thought the hot dog wasn’t going to live up to the hype either. Not the case. This hot dog was AH-MAZING and I never would have ordered all the toppings that came on The Original. We arrived right before noon and it was already getting crowded, but if you’re not in a rush to be somewhere it’s worth the wait. There was plenty of seating upstairs, and they’re very generous with their pours!

The Kitchen

The restaurant’s location along the Chicago River was a short walk from where our boat tour docked. This American Bistro’s changing menu follows a farm to table approach. The food and service were great. We didn’t feel rushed to give up our table and were able to sit and relax before heading out to explore more of the city.

The Kitchen is located in the brick building on the left.

Where are your favorite places to go in Chicago? Share your recommendations in the comments and don’t forget to follow @mywealthroad for more “Roads to Roam” features.

“Travel is the only thing you buy that makes you richer” – Unknown