Happy Tuesday, everyone! Pete and I got back from a long weekend in Chicago Sunday afternoon and he practically had to pry me from our hotel room on the way out – I wasn’t ready to leave! But then again, when am I ever? While the trip was last-minute, my never-ending list of places I’m dying to eat and drink at in Chicago was raring to go!

We inadvertently found ourselves on a Chicago rosé crawl of sorts Thursday afternoon (I like to think this is a step up from the pub crawls we frequented back in college) and for the sake of spontaneity, we tossed all other plans aside and just went with the flow. Totally unplanned, but totally worth it.
Let’s not waste any time – below are my top 5 places in Chicago to indulge in a glass of the good stuff!

First up, The Hampton Social! From their signature pink “Rosé All Day” signage to their Montauk-inspired sitting area – the entire restaurant is an Instagram (or three) waiting to happen.

Their goal is to bring The Hamptons to the city of Chicago (the River North neighborhood, specifically) and though I’ve never been, it has me longing to explore the East Coast further!
If you’re in this for the long haul, fueling up for the day ahead will be key!

They offer up 1/2 price glasses of their rosé of the day and their wood-fired pizzas Monday through Friday from 3-6, so keep that in mind if (more like when) you’re planning a crawl of your own!

Pete raved about the Maine-style Hampton roll and I’ve never been one to turn down a perfectly seasoned basket of shoestring french fries.Next stop: London House, located on Wacker and Michigan Avenue in the heart of the hustle and bustle of the city. The venue boasts breathtaking views of the city and a healthy mix of locals and out-of-towners. I highly recommend you snag a front row seat along the glass balcony like we did!

A little farther south on Michigan Avenue you’ll find the open-air terrace that is Cindy’s Rooftop. The restaurant showcases panoramic views of Millennium Park, the Art Institute, Lake Michigan and beyond – a testament to everything Chicago encompasses! (how gorgeous is this shot Katie took?)

The wait to get upstairs was worth it, but if you have the opportunity to get there early to avoid the crowd (and get the perfect Insta snap)…do it! Better yet? Make it your first stop!
Still with me? Make your way to City Winery on the Chicago Riverwalk and order a carafe (or two) off their extensive wine list. We opted to sit at the bar stool seats facing the water so we could watch the boats coming and going, and much like Hallie promised, it did not disappoint!

Side note: Growing up, we would make a yearly trip down to San Antonio to visit my Nana and Papa Colonel and spending time on the Riverwalk was always my favorite! We never missed the opportunity to stop in Kangaroo’s Court and enjoy a slice of their world-famous cheesecake with the boats along the river creating a picturesque backdrop. The scene at City Winery offered up a bit of familiarity in that sense, which I loved!You’re probably beyond ravenous by now! (anyone else always thinking about their next meal?) I suggest you make your way over to Lincoln Park for dinner to cap off what’s sure to be one of the best days you’ll have all summer long.

I’ve sung the praises of Summer House Santa Monica before (remember last summer?) and after discovering they have an entire cart dedicated to the pink water we all know and love, it’s the perfect spot to round out a rosé crawl.
If you aren’t looking to call it a day/night just yet or you’re working to build your savings, I’m a big proponent of creating your own patio party! Invite a few friends over and encourage everyone to bring a bottle to share with the group (bonus points for anyone who brings a cheese plate and accompaniments).

Whether you live in Chicago, are planning to visit soon or are mapping out your summer in your own city, I think it’s important to note it’s all about who you’re with!

Last minute tidbits: Mix up the order to suit your needs/schedule, have your uber app at the ready if walking from place to place isn’t an option, and if you’re venturing out with a large group, the Venmo app is great for divvying up shared tabs so as not to cause a huge mess for your server!

If you head out on a  rosé crawl of your own over the summer, tag me on Instagram or share with me on Snapchat (jessicazimlich)!

Cheers to the season, my friends!

Find more on Chicago here.

Third photo via The Hampton Social, sixth photo via Katie Cassman.