You know how much I love my city. The city’s energy, vibrant colors, and pure beauty captivates me. It fuels me to know every corner, the best cocktail, coffee, summer activity, winter activity.. you name it! With that, I made you guys a weekend itinerary with my top recommendations during the spring!
I want to get more organized with my guides and where better than to start than my very own city. Chicago is perfect in the spring and while I have made a few guides to date, I want to share tailored guides depending on the season and who you are with. I also want to share guides on what to do in Chicago for one weekend and a week! More to come, but I promise I’ll share all of these posts soon.
You’re in Chicago for a weekend. THINK: Thursday night until Sunday night. A weekend trip. You want decadent cocktails, delicious food at an Instagram worthy restaurant, photo opps galore and the best city views Chicago has to offer. You want to splurge but not too excessively because it’s all about #balance. GOT IT. I am your GIRL when it comes to making the most out of your trip! Check out my itinerary below for my top recommendations for a weekend in Chicago with a group of friends or significant other! *NOTE this itinerary is made for early spring so not all activities will be outdoor friendly (Chicago weather, you’re my best worst friend). Last April it was 75 degrees and sunny, so this is what my itinerary is based off of!
Visiting Timing: End of April – Early June
Who are you with? 1-3 friends OR a significant other
Have you been to Chicago before? Maybe once or twice.. you are down for some touristy things but want to go where the locals mingle too.
What are your interests? You love to walk, you love skyline views, good cocktails and authentic GOOD food. You are girly at heart with a love for a pink aesthetic and live (thrive) off of coffee.
Your Itinerary
THURSDAY
6 PM: Arrive to Chicago! Welcome! I AM SO HAPPY YOU ARE HERE.
8 PM: Start off Chicago strong with deep dish pizza at Lou Malnati’s in Gold Coast (my favorite location!) *Make a reservation in advance, it gets busy
10 PM: Fancy cocktails at Z Bar Chicago. Chill on the rooftop of the Peninsula Hotel that over looks the mag mile! *Make a reservation and request a table with a few!
11 PM: Night cap at Drumbar. Indoor and outdoor seating with pretty views of the city, close by to Z Bar (you can walk!) and the DJ’s here are GREAT. I am a fan of their Cosmo.
FRIDAY
9 AM: Breakfast at the Allis Chicago. Photo opps galore at the Allis and one of my go to recommendations! *Make a reservation!
11 AM: Stop by the Bean for photos
12 PM: Walk through Millennium Park, and stop by Buckingham Fountain for photos
1:30 PM: Stop by Cindy’s at the Athletic Association Hotel for a small bite and drinks while overlooking everywhere you just walked through! Aerial views for the win!
3 PM: Chicago Helicopter Tour! I HIGHLY RECOMMEND and worth the splurge!!
5 PM: Coffee at Sawada Coffee (on your way back from Chicago Helicopter experience) as a little pick me up!
6-8 PM: REST
8 PM: Dinner at Montaverde. Back in West Loop. If you love pasta like me, you must stop by Monteverde. Their menu is amazing. *You must make your reservation in advance
10 PM: Drinks at the Darling. Walking distance from Monteverde! It is a new speakeasy and one of my favorite bars in Chicago! *Reservation recommended but not needed on the second floor
Midnight: IF you’re feeling up to it, buy tickets IN ADVANCE to the Aviary for the most Instagram worthy cocktails you will ever see. A pricey ticket but worth every penny!
SATURDAY
10:30 AM: Brunch at Three Arts Club Café. Pretty sure I have shared this gem in a million posts but get here at 10AM to guarantee a good seat with no wait! If you like to brunch in a beautiful room, this is your JAM. *They do not take reservations
12 PM: Walk on Astor street. Take in the beautiful homes and architecture on Astor Street. Hugh Heffner lived in his bachelor pad here along with other stars and celebrities.
1 PM: Walk (or Uber) over to the LincolnPark Conservatory and Lincoln Park Zoo. They are neighbors so you can do both while cruising through Lincoln Park!
4 PM: Drinks at the J Parker. Skyline views! Weather permitting, the rooftop is a lot of fun with great views of the lake and skyline!
6 PM: Dinner at Etta in Wicker Park. Possibly the best overall meal I have ever had. *Make a reservation
9 PM: Drinks at the Green Mill. JAZZ CLUB! Hop in an uber and grab a table at the Green Mill. A Chicago Classic for sure!
SUNDAY
10:30 AM: Pick up a coffee and coconut cake donut from Stan’s Donuts
11 AM: Rent divvy bikes downtown and ride along the lakefront path up until you get to Fullerton
12 PM: Snap photos of the skyline at Fullerton Beach!
1 PM: Return your Divvy, grab lunch at LUX Bar in Gold Coast on the patio *great people watching spot!
2:30 PM: Walk (or uber) to Michigan Avenue Bridge and snag tickets for an architecture tour (90 minutes long!)
5 PM: Pack Up ☹
6 PM: Leave for the airport (8PM flight!)
Alternative options
Instead of a boat tour, check out the Sky Deck at the Willis Tower
Instead of coffee at Sawada, grab a coffee from Limitless Coffee and Tea
Ditch the pasta and go for sushi Tanoshii in West Loop
Drunk burritos at Fat Baby Tacos. You’re welcome.
Check out more of my favorite rooftop bars here!
Thanks for visiting my favorite city!
XO.
Lex