A non-touristy Weekend Guide to Chicago… so you can see all the hidden gems!

We may be bias, but Chicago is one of THE BEST cities to visit in the country! We highly recommend summertime, but regardless what season, there is so much to do, see, and eat, that you can easily fill up a day going from place to place, or simply leisurely walk around from gem to gem! Chicago is filled with many unique neighborhoods and each has their own unique vibe, I’m sure you’ll find a place to love! There is of course Millennium Park, the “bean” and Navy Pier, but there is so much more to Chicago than these tourist hot topics.In this post, I’ll guide you through the Lakeview, Lincoln Park, West Loop, Logan Square, and Wicker Park neighborhoods. One tip for any neighborhood is if you don’t like waiting in lines, we would recommend to make a reservation for the restaurants you really want to go to. But if you don’t there is plenty to walk around and see while you are waiting. Here are our top recommendations for a weekend in Chicago:

Where to stay:

The Robey – this eclectic, new hotel is located in a young, residential neighborhood in Wicker Park. There are a lot of great restaurants and shops within walking distance, and the Blue Line to take you downtown or to different neighborhoods.

Hotel Lincoln – an older, charming hotel in Lincoln Park with some of the best views of the park, water, and city. A perfect location in our book!

Willows Hotel – This hotel is tucked away in a residential street, and will give you a “living like a local” feel. This is a great neighborhood in Lakeview, again close to many restaurants, shops, and the lake.

Friday Night 

  1. Start at The J. Parker rooftop for early drinks. If you are staying at the Hotel Lincoln, you just need to go to the rooftop! You’ll get the best views of the city here! You can see the beautiful park, Lake Michigan, and the city skyscrapers. It’s a can’t miss view of Chicago. We’ve been known to frequent this rooftop with a glass of prosecco during happy hour

j parker

2. Parlor Pizza/ RM Champagne Lounge/ Soho House: There are THREE amazing restaurants in the West Loop right next to each other, so we’ve included them all depending on your taste. West Loop  has been an “up and coming” neighborhood, just west of downtown for a few years now and is pretty much at its prime. The used-to-be-factory area is now filled with trendy restaurants, breweries, and cute shops.

Parlor Pizza Bar:  A casual delicious pizza place with lots of outdoor and rooftop seating. The vibe is young and energetic, great for groups, and features tons of delicious pizzas. They even have a location in Wicker Park. You can’t go wrong here!

parlor pizza

RM Champagne Salon: We love this charming outdoor patio, and combined with a glass of prosecco makes for a perfect night! A french inspired bistro tucked behind a small cobblestone alley has a modern-romance feel. We go for the drinks and they also have great seafood, flatbreads, and various entrees.  


The Allis at Soho House: Soho House is membership based for those in creative industries, but the Allis is a lounge/ bar on the first floor and open to the public. A step into elegance, with enormous chandeliers, velvet couches and chairs, and rich wood panels. Trust us, you will feel #expensive here. The dishes are best for sharing.  


3. End the night at Punch Bowl Social: There’s so much to do here and great for groups too! On the first floor you’ll find a retro 50s style bar and then make your way upstairs for the activities! There’s bowling, virtual reality, board games, karaoke and lots more. We recommend making a reservation for the activity you want to do and then explore around the different rooms and bars. Punch Bowl does get crowded so you can always go in the daytime too. Don’t forget to use the photobooth before you leave. 




  1. Maison Parisienne: head to the cutest french cafe for a lowkey breakfast of coffee, pastries, and french-inspired dishes. This is a casual place where you can order at the counter and go, but we would recommend grabbing a seat in their cozy, California-chic setting. We die for the almond croissant, but would recommend their quiches as well. Their pastries and coffee bar are some of the freshest we’ve had!

French Cafe Bar Stools.jpg

  1. Hang Out at Lake Michigan: where else can you get a beach right next to a big city? Lake Michigan and the beach is our favorite weekend place in Chicago, and just a hop, skip, and jump away from the delicious restaurants and busy streets of the city. You can plan on a relaxing day sunbathing, or head to the North Ave entrance where it is packed with energy from volleyball games, drinks at the boat (a restaurant/ bar on the beach), kayaks, jet skis, and the Shore Club. If you are looking for a cabana and to be waited on hand and foot, check out the Oasis at the Shore Club.  
  2. Visit the “Greetings from Chicago” mural: an iconic mural in Chicago full of color and a perfect photo-op! This sign is located in the Logan Square neighborhood.

Chicago Sign.jpg

  1. While you are in Logan Square, stop by Margie’s Candies for a good old fashioned sundae with hot fudge and caramel candies. It has an adorable 1920’s diner vibe, and a local favorite and they have a location in Uptown too!
  2. Go to Big Star for dinner: this is an absolute must in our book! They have a huge outdoor patio you can spend a few hours sipping on margaritas and people watching (it’s so good in this area!). Their mezcal margarita is a go-to, and they feature tons of delicious tacos including fish, pork, steak, and vegetarian option. Even meat eaters will love their vegetarian tacos, they are that good! There’s now a location in Wrigleyville too, so if you catch a Cubs game, swing by for a spicy margarita.33618529_175138976659361_4943925356798148608_n
  3. If there is a wait at Big Star (which there usually is)  go right across the street to The Violet  Hour.  You might not notice this place at first because the door blends into the wall, and they paint the wall a new mural all of the time, so I can’t even tell you what mural to look out for! It’s a speakeasy with some of the best cocktails in the city, and in true speakeasy fashion, they don’t allow your phones to be out.
  4. End the night at Whiskey Business, a rooftop bar not far from the Wicker Park Big Star with loud music. They have an array of whiskeys, but if you’re not a whiskey drinker they also have a fun selection of cocktails. Chicago is all about the rooftops in the summertime!


  1. Brunch! The brunch scene in Chicago as there are so many delicious places to choose from. We would recommend “Toast” in Lincoln Park or Buck Town, a cozy spot with delicious, fresh food. Andrea almost always gets the scrambles here, and you will not leave hungry! Another favorite is “Kenela” in Old Town, Lakeview or Wicker Park. It’s another cozy spot with a cute atmosphere, and we recommend the french toast sampler. Image 2018-08-04 at 12.56.16 PM.png
  2. Walk around Armitage Street and visit all of the shops before you head out. This is within walking distance from Toast (Lincoln Park location) and a perfect low-key activity to do before you hope on a plane/ train/ bus/ automobile back home!

All of these spots will give you a great taste of everything wonderful Chicago has to offer, and we would recommend you to wander around any of these spots above to see what else the city has to offer. There are so many more neighbors and places to explore, so if you’d like additional recommendations or have questions just ask!

We won’t be doing you justice on the city without addressing a question we get asked a lot from out of towners; is Chicago safe? Our answer is yes. We are very comfortable walking around the places we’ve mentioned to you. Like any other city, there can be unsafe places, but in Chicago, you won’t just turn a corner and walk into an area where you would question your safety. You would have to go out of your way to get to these places. Like get in a cab, ask them to drive for 15 minutes and willingly get out of the cab.


Hope you love Chicago as much as we do!

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