5 Things to Do This Weekend In Chicago

5 things to do this weekend in chicago, a lily love affair, chicago blogger, shein black chiffon dress, zac posen bag, miu miu sunglasses, lincoln park zoo

I hear you. It’s Monday and we’re already talking about Friday. Totally understood. But, hear me out.

It seems Summer will officially arrive here in Chicago this week.  The city is so alive when the warm weather breezes in. With this week and weekend consistently in the 70-80’s (fingers crossed the warm weather God’s don’t change the call), we wanted to share 5 things to do this weekend in Chicago that will help your heart sing and truly enjoy all that this city has to offer in the Summer months.

Whether we live locally, or are traveling in from out of town, these 5 activities will be friendly on your wallet and your soul :):

1. Lincoln Park Zoo

If you have never been, you have to move a visit to the Lincoln Park Zoo to the top of your things to do this Summer in Chicago. Whether you just want to grab coffee and take a relaxing, scenic walk with a girlfriend through the park or want to pack the car with all the kids, the Zoo has something to offer everyone.

And, y’all, it’s completely FREE. Yep, 365 days a year – FREE. You can enjoy lunch at one of the several on-site cafes, take in the breathtaking views of the city, or stop by the half dozen plus exhibits. Here is a full PDF guide to help you plan your visit.

It’s worth noting, we also took these shots at the zoo last weekend. 🙂 Get out there and enjoy the city and all that the zoo has to offer.

2.  Brunch at Cindy’s Rooftop 

One of my all time favorite Chicago rooftops is Cindy’s, atop the Chicago Athletic Association Hotel.  Not only are both the food and cocktails to-die-for, the view overlooking Millennium Park and the lakefront are unforgettable.  With the perfect 75 degree forecast this weekend, gather your grilfriends or hot date and snag yourself a table at Cindy’s.  Check out our post with Caldrea for more of our experience at Cindy’s.

3. Green City Market

Chicago’s largest and first year-round sustainable farmers market, Green City Market provides a marketplace for purchasing sustainably grown food and connecting farmers and local producers directly to chefs and the greater Chicago community.  I have not had a chance to enjoy the market yet myself, but I have been dying to try!  It’s on my list of things to do this weekend. Be sure to follow along on InstaStories and I’ll share our experience!

With over 50 local vendors, shop fresh produce, baked goods, fruits, cheese and enjoy a lovely fresh flower mart.  Here is a complete list of 2017 vendors.  Enjoy!

4.  Lunch at City Winery

When the weather warms up, City Winery is one of my other favorite outdoor places to enjoy lunch, a good cocktail and some truly fabulous people watching.

With City Winery situated along the riverfront walkway, you can enjoy all of activity taking place on the river and the take in the incredible views of the city.  Can’t swing lunch?  Check out their line-up of great live musicians and enjoy and evening on the town for dinner.

5.  Sail Chicago

See Chicago like you never have before with a a private sailing lesson or tour. Escape the noise and the bustle of the city without leaving your zip code.  Chicago Sailing offers a variety of boats and activities that make getting off land and onto the lake easier than ever.  With lessons, charters, and rentals we can help you experience the city and the lake like you have never seen them before.  Our fleet of over 20 vessels ranging from 22′-53′ and staff of US Sailing & USCG certified instructors and captains means you will always have a enjoyable and safe experience on Lake Michigan.

I had an opportunity to experience Chicago sailing with Helly Hansen last Summer during the National Offshore One Regatta and it was an incredible way to experience the lake and this fabulous city.

Save 33% on rentals now through May 20th!

What would be on your list of 5 things to do this weekend in Chicago?  I’d love to hear some of your favorite to-do’s!  Add your comments and I’ll credit you in the next round of posts!

5 things to do this weekend in chicago, a lily love affair, chicago blogger, shein black chiffon dress, zac posen bag, miu miu sunglasses, lincoln park zoo

5 things to do this weekend in chicago, a lily love affair, chicago blogger, shein black chiffon dress, zac posen bag, miu miu sunglasses, lincoln park zoo

5 things to do this weekend in chicago, a lily love affair, chicago blogger, shein black chiffon dress, zac posen bag, miu miu sunglasses, lincoln park zoo

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5 things to do this weekend in chicago, a lily love affair, chicago blogger, shein black chiffon dress, zac posen bag, miu miu sunglasses, lincoln park zoo

5 things to do this weekend in chicago, a lily love affair, chicago blogger, shein black chiffon dress, zac posen bag, miu miu sunglasses, lincoln park zoo

5 things to do this weekend in chicago, a lily love affair, chicago blogger, shein black chiffon dress, zac posen bag, miu miu sunglasses, lincoln park zoo

5 things to do this weekend in chicago, a lily love affair, chicago blogger, shein black chiffon dress, zac posen bag, miu miu sunglasses, lincoln park zoo

5 things to do this weekend in chicago, a lily love affair, chicago blogger, shein black chiffon dress, zac posen bag, miu miu sunglasses, lincoln park zoo

5 things to do this weekend in chicago, a lily love affair, chicago blogger, shein black chiffon dress, zac posen bag, miu miu sunglasses, lincoln park zoo

5 things to do this weekend in chicago, a lily love affair, chicago blogger, shein black chiffon dress, zac posen bag, miu miu sunglasses, lincoln park zoo

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27 Comments

  1. May 15, 2017 / 6:56 am

    You’ve already given me a reason to want it to be the weekend again! All of these sound like SUCH fun things to do!

    The Adored Life

  2. May 15, 2017 / 7:30 am

    I would be all about that free zoo!! My kids would love that! I’m also loving your pretty dress and these gorgeous photos!

    Brooke
    Pumps and Push-Ups

  3. May 15, 2017 / 10:51 am

    I went to Green City market this weekend! That market is my absolute favorite, not to mention ALL of the food choices are amazing!

  4. May 15, 2017 / 11:43 am

    I totally could have used this a month ago! But I still had a great time – it was my first time & Chicago was such a great city!

  5. Heidi
    May 15, 2017 / 1:00 pm

    Such gorgeous shots Anna and so many great reminders of all the things there are to do in Chicago in the summer! You look absolutely beautiful! Can’t wait to see you soon 🙂

    Heidi || Wishes & Reality

  6. May 15, 2017 / 1:04 pm

    Chicago is my favvvvvv in the summer so I love love this list! Cindy’s is the BEST in the summer. This makes me miss the city so much!

    Love it!
    xoxo
    Krista
    http://www.hundredblog.com

  7. May 15, 2017 / 4:21 pm

    What a great guide to chicago! You look so pretty!

  8. May 15, 2017 / 4:44 pm

    I’ve always wanted to take my mom to her birthplace. Having some fun while we are there is on my to do list!

  9. McKenna
    May 15, 2017 / 5:48 pm

    Anna you look amazing in this dress! Love the style and fit of it! Chicago is definitely a city I would love to visit one day! Happy Monday girl! xo
    McKenna
    stylewaltz.com

  10. Joline
    May 15, 2017 / 7:56 pm

    Chicago is one of my favourite cities! There’s so many things to do. Now there are 5 more reasons to go 🙂

  11. May 15, 2017 / 10:19 pm

    It’s been a few years since I’ve been to Chicago. The sailing idea sounds so awesome! The color of Lake Michigan always gets me, so blue and pretty!

  12. May 15, 2017 / 10:31 pm

    A rooftop brunch sounds perfect, and that outfit is so pretty!

  13. May 16, 2017 / 11:21 am

    I love all these fun ideas, makes me wish I was in Chicago! On another note, this look is so pretty! Love the details on your shoes!
    – Jessica
    Miss Moore Style

  14. May 16, 2017 / 11:23 am

    Fun! I’m headed to Chicago in a couple weeks, so this is great! xx

  15. May 16, 2017 / 5:01 pm

    I am honestly so close to Chicago! I definitely need to make it up there this summer.

    xo,
    Steph
    @trendyinindy || trendyinindy.com

  16. May 17, 2017 / 8:27 am

    SO glad you shared this list, I’m headed to Chicago in August and I’ve never been, so I’m definitely taking note of your recommendations!

  17. May 17, 2017 / 4:46 pm

    I’ve been wanting to visit Chicago, will have to bookmark your post for a future trip there!! Thanks for sharing!

  18. Courtney
    May 17, 2017 / 8:16 pm

    Such a gorgeous chic look!! I love your bag! Thanks for all the tips and spots, I’ll keep these in mind next time we visit the Windy City.

    Xo,
    Courtney whatcourtwore.com

  19. May 21, 2017 / 4:04 pm

    Cindy’s is seriously the best place ever!

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