Chicago Summer Bucket List 2018

It’s the best time of the year in the city, and it’s why we take on winter every year.  Chicago Summer is a non-stop party if you use your time wisely.  Enjoy our bucket list below to celebrate all of the fun!  Soon, we’ll be releasing our Chicago Summer calendar.  For now, enjoy the bucket list!

1. Toast with Rosé all Day

Are Summer Fridays back?  So is rosé all day!  The Chicago Eater pulled together a guide of all of the best places to toast with rosé in the city, and we’re in love.  If you’re looking for a little rosé all day bar crawl, might we suggest starting at Cindy’s downtown?  It’s the perfect spot for lunch & a glass.  From there, head on over to London House for the best views of the north side of the Loop & river.  Then pop over to The Hampton Social so you can get the quintessential picture by the ‘Rosé All Day’ sign.  Glam it up Upstairs at the Gwen Hotel for a drink while you soak in the views.  Time to head over to Gold Coast.  Were you a fan of the old Cedar Hotel?  It’s back and part of Somerset, which has the perfect patio for a drink.  Petit Margaux is also a beautiful spot.  Grab another photo opp at 3 Arts Club Cafe before making your way up north.   Depending on where you live, head for an ‘afternoon cap’ at Summer House Santa Monica or Mordecai.

2. Snuggle under the Stars at Movies in the Park

What’s Chicago Summer without movies in the park?  The Chicago Park District hosts movies in the park across the city all summer long.  Movies kick-off in June and run through the end of August.  Their guide is super easy to search for any location or time you desire.  Gallagher Way at Wrigley Field hosts their own movies in the park as well, which they have a schedule for here.  Both events are free; however, there is no alcohol allowed at Gallagher Way since they sell it on site.  Additionally, you can rent a chair for $20 each at Gallagher Way, but it’s not required.

3. Grab Something Fresh at Green City Farmer’s Market

If you haven’t been yet, the Green City Market in Lincoln Park is the mecca of all farmer’s markets in Chicago.  It’s the place to be on Saturday mornings from 7 am to 1 pm.  They have the most gorgeous flowers although they typically sell out, so get there before 8:30 am if you want blooms!  When you go, grab a crepe from Abby’s Crepes and enjoy the scenery.  Green City is also in the West Loop on Saturday mornings s and Gallagher Way at Wrigley Field on Thursday nights.  The city of Chicago also hosts farmer’s markets all over the city nearly every day of the week although Wednesdays, Thursdays, Saturdays, and Sundays appear to be the most popular.  You can check out their guide for a full schedule.

4. Dine al Fresco

Being outside as often as possible is a must-have during Chicago summer.  The Chicago Eater and TimeOut Chicago have extensive lists.  There are some great rooftop restaurants to try – Noyane has been on our list for a while and Mahalo is a perfectly instagrammable spot!  Rooftop happy hour is a must-have on our list.  Cindy’s tops our list again along with Drumbar.  There are also plenty of outdoor bars and restaurants all over Chicago!  Parson’s Chicken & Fish, Duck Inn and Tied House top our list of outdoor restaurants this summer.  On a Saturday afternoon, grab your furry best friend and head to a dog-friendly patio or a bar with giant outdoor games.

5. Take a Road Trip

Although Chicago is one of our favorite places to be in the summer, you could always take a weekend away.  Thrillist pulled together a great list of the best weekend getaways (hint: Lake Geneva, we’re looking at you!) as well as a handful of underrated getaways, too.  There are so many gorgeous wineries in northern Michigan and Wisconsin – it makes for the perfect girls’ trip or couples’ weekend getaway!

6. Hit the Beach

Chicago beach season officially kicks off Memorial Day Weekend.  The Chicago Park District publishes a list of all beaches so you can find the one closest to you.  We personally love Oak Street Beach, North Ave Beach and Montrose Beach, which are all a Divvy ride away.  TimeOut Chicago also captures some of Chicago’s best beaches.  If you get the chance to catch a ride on a boat, don’t think twice and take it!

7. Enjoy the Street Fests

Street fests may be one of the best parts of Chicago summer.  Every weekend, you can find a different street fest in a different neighborhood with local food, music, and beer.  They’re casual and the epitome of a chill summer Chicago day.  The full schedule is on Choose Chicago’s website.  Some of our favorites are the Sheffield Garden Walk and the Taste of Randolph.  No matter what you choose, you’re certain to have a good time!

What are your plans this summer?  Share with us below!

Meet Jen

I’ve always had a love affair with creation. Since I was a child, I handmade my gifts or combined toys to design something new. Fast forward twenty years, and I’m still making my gifts every holiday and designing new ways to do things.


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In order to grow my small business, I earn revenue in a few different ways. I publish sponsored posts from time to time, which are always labeled. Sometimes I earn an affiliate commission on the sales of products or business resources I link to. I only feature items I genuinely love and want to share. Thank you for reading and supporting my small business!

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