Travel Guide: Weekend in Chicago

My parents and I visited Chicago for Father’s Day weekend and my Dad’s birthday. Chicago is a very walk-able city and it’s the best way to see (and eat) everything it has to offer. I hope this travel guide is helpful while you plan your trip!



Whether you are flying into O’Hare or Midway there are a couple options for getting into downtown Chicago.

By Uber/Car – Going to the city from O’hare can take anywhere from 20 minutes to over an hour depending when you land. Midway is just a little closer and can take around 15 minutes with no traffic. I suggest using google maps to check the traffic/travel time for the time and day you will be departing those airports.

The L

Short for “elevated” this is the city’s transit system similar to the subway or metro in other cities. Some portions of the L run 24 hours a day and it’s a very affordable option.

Blue Line – This will take you all the way into the city directly from O’hare. I took this going to O’hare once during rush hour for only $2! It will take about an hour from downtown Chicago.

Orange Line – This line will take you right into the city from Midway in roughly 30 minutes.


We stayed at the Cambria Hotel & Suites Magnificent Mile. This cute hotel has an awesome rooftop bar plus great nearby restaurants and shopping! 

I also recommend the Sofitel hotel, where I stayed during an earlier trip to Chicago I took in March. Also located along the Magnificent mile, Sofitel has great access to shopping and many of Chicago’s fun activities. 

For hotels, I suggest these areas. They are very central to most of the fun stuff to do in the Windy City!

  • Magnificent Mile / Streeterville
  • River North
  • The Loop / Millennium Park






Stroll the Chicago Riverwalk. Also called the city’s “Second Lakefront,” this pedestrian path contains a handful of restaurants and boat tour companies. My mom and I walked along the Riverwalk at night on our way back from dinner. It was a stunning walk with all of the buildings illuminated reflections on the river.

Go on an Architectural Boat Tour. My Dad booked with Wendella for Chicago’s Original Architecture Tour and I surprisingly LOVED the narrated 90 minute tour. The buildings in Chicago are so unique and it was very interesting to hear about them from our tour guide, Wendy (she was awesome). 

Go to a Cubs Game at Wrigley Field. My parents and I love baseball and Wrigley field is an iconic and historic stadium worth going to. I made sure to try a Chicago-style (DIY) Hot Dog while I was there, too—because what goes together better than baseball, hot dogs and beer? 

Visit one of the museums in Museum Campus. I will admit that museums aren’t the first thing that comes to my mind when I think of Chicago, but visiting a few is great activity to check out while you are there. In addition to the museums in the Campus, the Museum of Science and Industry is just a few minutes south down Lake Shore Drive—Dad loved the Submarine exhibit there.

Get the ever-popular instagram at the Willis Tower Skydeck. I was SO excited for this as I’d seen pictures of the Skydeck all over social media and wanted to experience it for myself. The Willis Tower (formerly the Sears Tower) had great views of the city from every side of the building. We waited in a short line to take a step out onto the “ledge”. I was initially so confident and ready for my picture but it was actually pretty terrifying! Did it for the ‘gram.

Take in the views from 360 CHICAGO and the TILT. Located in the John Hancock building, the 360 CHICAGO observation deck had, in my opinion, the best views of the city. I made the trek to the top during a trip with friends and we enjoyed the 360 degree views. I gladly volunteered to be videographer as they tried the TILT—a “ride” that literally tilts you over the city from the 94th floor. 

Visit Millennium Park and the Cloud Gate aka the “bean.” That’s right, it’s not actually called the bean. Make sure to grab your picture with this Chicago icon and wander the park showcasing other interesting artwork and sculptures.


Full outfit details here



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Spots we really liked:

  • Beatrix – We grabbed breakfast here before a long day and it was AMAZING. Mom and I split the Wonderful Egg-White Omelette and the Light & Fluffy Lemon Pancakes—both were absolutely delicious. They have a few different locations in the city.
  • The Hampton Social – I went here with Mom while Dad was at the Metallica concert—yes I just said Metallica concert. It’s got a Hamptons beach-y theme with the cutest “Rosé all day” ivy wall in the patio room. Although I am not a big fan of frozen drinks I went with their frosé and I’m glad I did. I was eyeing the King Crab Dip and the server assured us it wasn’t as heavy as we might think. The dip was a great blend of cheese, spinach, artichokes and crab served with toasted polenta bread. YUM! 
  • RPM – I’ve been to RPM a few times here in DC but my parents LOVE Italian food so I really wanted them to try this great restaurant—plus Mom loves Giuliana. As expected, my parents raved about the food as we all enjoyed the delicious homemade pasta and truffled garlic bread. You also can’t leave RPM without trying their mini Sicilian Cannolis for dessert.
  • Cindy’s Rooftop Restaurant – Located in the Chicago Athletic Association Hotel this restaurant has stunning views of Lake Michigan and Millennium Park. Make sure to grab a reservation ahead of time as it’s always super busy! My friends and I enjoyed a few cocktails on their balcony.
  • Eataly Chicago – With locations also in NYC and Boston, Chef Mario Batali’s Italian marketplace is a great spot to pop into after a long day of shopping or walking around Chicago.
  • Giordano’s – No trip to Chicago is complete without a slice of deep-dish pizza. I love a hot slice of thin-crust but I was a big fan of the this “stuffed pizza” when I gave it a try. Giordano’s has locations all of the city and you can even grab a frozen one to take home! 
  • The Purple Pig – This place is on my list for my next trip to Chicago. The menu is made up of various Mediterranean small plates.
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The Hampton Social


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