How to spend a summer weekend in Chicago


Chicago is a great place to be when it’s warm, sunny, and looks like this. And with August 1/3 of the way over, summer in Chicago will be over before we know it. I had a friend in town last weekend which was a perfect reason to play tourist in this beautiful city. So whether you live in Chicago or are planning a visit, here’s a list of what we did last weekend and some of my favorite spots and things to do.

Processed with VSCO with a6 presetAllis/Soho House Chicago 

My summer weekend in Chicago

Thursday night: Dinner at Coalfire (the best pizza) and dessert at Jeni’s.
Friday: Tacos and margaritas at Big Star, walk/shop on Damen, pool at Soho House, dinner at Green Street.
Saturday: Brunch at Beatrix, walk/shop Lincoln Park, coffee at Le Pain Quotidien, evening stroll through the Gold Coast, dinner at Le Colonial, drinks at Pump Room.
Sunday: Brunch at Cindy’s, walk/shop downtown, dinner at Tango Sur.
Monday: I was sure my friend was leaving Monday morning but missed the PM on her itinerary, so we spent the day a the pool and picked up Mak before her flight. I would not recommend Mak unless you live here or are in town for at least a week and need a relaxing night in. It’s good but it’s take-out.

Processed with VSCO with a6 presetGreen Street Smoked Meats

Things to do

The pool or beach: Lay out, paddle board at Chicago SUP, or bike along the lake, or consider a stay at Soho House where members and hotel guests have access to the rooftop pool
Bike riding: Rent a divvy and cruise around the city
Water taxi or architectural tour: A budget-friendly way to get out on the lake without chartering a boat
Markets: Randolph market, green city market, street festivals, and concerts in the park
Watch some fireworks: Every Wednesday and Saturday at Navy Pier
Movies in the park: They’re fun and free
Museums: We have plenty of them
Shop: Michigan Ave, Gold Coast, and Armitage in Lincoln Park have great shopping
Walk: Go for a stroll through the Gold Coast, Lincoln Park, and along the lake

Cindy’s Rooftop

Where to eat and drink

Cindy’s: Maybe the best rooftop brunch and best view in the city (note: the platters come in half portions)

West Loop
Green Street: Enjoy some BBQ on a patio under twinkle lights
Sawada Coffee: They have the best iced almond milk lattes and are in the same building as Green Street
Girl and the Goat or Little Goat: On the heavier side but so good
Avec: Walk-in only, so get there early or put your name in and grab a drink at Lone Wolf (and please order the bacon wrapped dates)

River North
Make a reservation at least a month out or show up really early and hope you get a table
Beatrix: Cute little brunch spot and easy to get into last-minute (excellent gluten-free menu)

Gold Coast
3 Arts Club: Put your name on the list, order a latte at the bar, and walk around one of the prettiest stores in Chicago
Le Colonial: Delicious Asian fusion. Request a spot on the patio or balcony!

West Town/Bucktown/Wicker Park
*These neighborhoods are all very different but are so close to one another that I’m grouping them together
Coalfire Pizza:
 I’m not a fan of deep dish but really love Coalfire’s thin crust pizza
Yuzu: Robata grill–order the seaweed salad!
Folklore: Tango Sur’s sister restaurant and the best Argentinian food I’ve had outside of Argentina
Big Star: Best tacos and margaritas in the city, and the patio can’t be beat. Get there early or put your name in and walk around for an hour or two.
Jeni’s Ice Creams: No explanation needed

Logan Square
Lula Cafe:
Great spot for brunch, dinner, or drinks
Parsons: The purple drink is basically a red wine slushy and they have frozé

There are so many neighborhoods and incredible spots in Chicago, so while this isn’t the most comprehensive guide, it’s a list of some of my favorite things to do. I almost included my favorite music venues but that needs its own post. I hope this list inspires you to get out in your city, try something new, or maybe visit Chicago!

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  • I’m so happy you posted this! My mom and I are taking the train from Milwaukee to Chicago this weekend. I’ll have to keep these spots in mind!

  • I will need to keep this list handy—I wanted to get to Chicago this Summer, not so likely to happen and I’m nearby, in MN. Prefer to fly since long car trips are not my thing, especially for just a wknd-ha. Thanks for sharing where to go and what to eat and see!

  • Love this! As someone who also lives in Chicago, I concur with all the things on this itinerary! Chicago has such a great collection of so many different types of cuisine that it makes it difficult to narrow down where to take out of town guests. Coalfire and Parlor Pizza are two of my favorites in Chicago (not a fan of deep dish either), but Pequod’s (Webster & Clybourn) is a great choice for those who want to try Chicago style pizza but isn’t so cliche as Lou Malnati’s or Giordano’s. Also, Tango Sur is my boyfriend’s favorite restaurant in the entire city – we usually end up going about 2x a month and actually went on the Saturday of this past weekend as well! I love the outdoor patio they set up in the summer, you lose that romantic candle lit vibe that the inside setting as but still was cozy and wonderful. I haven’t been to Parson’s yet but have heard so many good things about their outdoor patio and frozen alcoholic slushies. Will need to plan on going soon! xoxo, Taylor

  • I was in Chicago for the first time for work a few weeks ago. I was secretly hoping I would see you since I’ve been a fan of your blog, your style, and the Everygirl for a while now. Unfortunately, I only got to stay in Chicago for one night but I really enjoyed it. It’s so clean, casual, and less populated than NYC which I found so refreshing. I’ve grown up in New York and I’m so over it.
    Hopefully, I’ll be back soon and get to try some of your suggestions. I love reading recommendations of places to visit from people that live in the city.

    1. Aww that is so sweet. Let me know the next time you’re here! Hope you enjoyed your one night in the city. I love NYC but chi is definitely a a bit more mellow.

  • is there a pool you recommend without a membership?

    1. The only one I know about is lakeview athletic club. You can get a 1 day pass for $25, which isn’t cheap (and I’ve never done it) but heard it’s a good one.