Plan Your Trip to Chicago with my Getaway Guide

  I love sharing tips and all the secret spots so our friends can enjoy the cities we love, and you’re my friend, so I hope this Getaway Guide comes in handy as you plan your trip to Chicago!

 Chicago is one of our favorite cities to run off to for the weekend, especially in the summer and fall months. It’s easy to grab my carry-on and go! Their subway system makes getting around town super easy and affordable.  Buy a day pass if you plan on location hopping, and you’re good to go.  Your subway ticket is good for both the subway and bus systems, and you can go literally anywhere on either.  

Downtown

  Like most cities, I prefer the little pockets of goodness found outside the downtown area, but there are a few must do’s in the heart of Chicago as well.  You can start at Wildberry Pancakes and Cafe for specialty pancakes as big as your face, then head cross the street to Millennium Park.  Wander from there to find stellar street views, flower gardens, and the infamous Bean.  You’re also only a couple blocks away from the Chicago Riverwalk which is a MUST SEE.  I definitely suggest taking a water taxi ride to see the city from the river; it’s way cheaper than a boat tour (it’s only like $4!), and you see all the same things!  Along the water, you’ll find great wine bars and places to sit and watch the sailboats pass by.   On a sunny day, it’s one of my favorite things to do.   You can also find paths that lead to tulip gardens and hidden grassy parks during the summer months. 

Views

  Just north of the Riverwalk is the best view of Chicago in my opinion: the Signature Room at 97th.  Y’all, it is phenomenal.  Grab a glass of bubbly and a hummus plate while you get a 360 degree view of the city.  (Side note, one of the best views is from the bathroom!).  You can also head just north and walk along the shoreline of Lake Michigan.  You’ll find a great skyline view, beautiful blue lake water, and a great path for a run or bike ride.

  Anyone who knows me knows I’m on the hunt for the local donut shop wherever I go.  I’ve been to a couple, but Stan’s in Wicker Park and off Michigan still takes the cake, and I legit visit every time I go. UGH IT’S SO GOOD, and the little shop is instagram worthy.  While you’re in Wicker, take a stroll to find eclectic little shops from boot boutiques to thrift shops and great brunch at The Bongo Room.

Lincoln Park

  One of my all-time favorite areas of Chicago is Lincoln Park.  I could pinch its cheeks it is so cute.  You can stroll along little side streets (and in my case take pictures of all the squeal worthy homes), but you HAVE to stop in at these two places:

  Summer House Santa Monica–its all things California from the vibe to the menu.  It’s the perfect spot for lunch or happy hour; it’s bright and open and oh so happy.  Homeslice: sit out back!  Such a fun vibe with twinkly lights, marquees, and a parked airstream where you can grab pizza and a beer.  They also have spunky cocktails and yummy salads.  

Pizza

Now, I know people take their Chicago deep dish seriously.  The staples are worth trying for sure (Giordano’s and Lou Malnatis), but I can’t lie—it’s not really my thing (I know, I know).    I love stopping at Eataly (identical to the ones in NYC) for Neapolitan style pizza, good wine, and canolis… and gelato and pasta and all the things.

Catch a Cubs Game

  Last but DEFINITELY not least, you are not experiencing authentic Chicago if you don’t catch a Cubs game (is anyone actually a White Sox fan?).  My husband and I love baseball, but even if it’s not your thing, Wrigley field is full of nostalgia, and the enthusiasm around Wrigleyville is contagious.  Win or lose, Chicago loves their Cubs; every game is packed, traditions are held dear, and the experience is all things Americana.     

  If you plan a trip to Chicago, drop in on Instagram and let me know if you find a new hot spot or if you enjoyed any of my faves!  

Happy Adventuring!
-a