Weekend Guide to Chicago in the Summer

I love putting together my “Best Of” roundups about Chicago for you guys, but I’ve also gotten a lot of questions about what I would prioritize the MOST. A weekend isn’t enough time to hit everything on my other lists, but you can still cover a lot of ground in this pretty city! Whether you’re the tourist or the tour guide, here is a list of my favorite things to fill a weekend in Chicago!

My Weekend Guide to Chicago in the Summer

1. Stroll along the Chicago Riverwalk

To me, the Chicago River is the most iconic spot in Chicago. You can be standing anywhere near it and you feel completely surrounded by CITY – a feeling you don’t get when you’re up in the neighborhoods mostly people actually live in! But instead of just standing on one of the bridges, you can find some steps anywhere between Lake Shore Drive and Lake Street, and walk right along the river. It’s all been redone, so it’s absolutely gorgeous. Grab an ice cream and sit on the steps – or head to City Winery for a glass of wine!

2. Architecture Boat Tour

*image via

Speaking of the Chicago River, the Architecture Boat Tour is a summertime MUST if you’ve never been on one. It’s the most beautiful way to see and learn about our famous architecture, and the tour guides are always super knowledgeable about the rich history behind it all. Plus, if you loved the movie My Best Friend’s Wedding, you can pretend like you’re Julia Roberts for a quick sec ?

3. Drinks with a view!

I always recommend LondonHouse and Cindy’s to anyone visiting from out of town. LondonHouse looks right over the Chicago River, while Cindy’s has an incredible view of Millennium Park… and both are sure to give you all the Chicago feels. You can also read about my other favorite Chicago rooftops here!

4. Walk around Millennium Park

This is probably the most touristy thing on the list, but I couldn’t leave it off! Sure, locals don’t hang around the bean on a regular basis, but there’s a reason we take all of our visiting friends and family to go see it. Despite being a popular tourist destination, it’s still an awesome piece of art! The way the skyline reflects off of every angle is pretty remarkable – and who can resist that photo op?! Plus, once you’ve gotten your fill, you can check out the Pavilion, Maggie Daley Park, and even walk down to Grant Park to see Buckingham Fountain.

5. Walk through the Green City Market and Lincoln Park Zoo

Typically, people who are visiting from out of town stay in the Loop, West Loop, River North areas – but there is SO much more to Chicago than that! If you want to see a little bit of real, normal Chicago life, I recommend swinging by the Green City Market. It’s an adorable Farmer’s Market in Lincoln Park full of local vendors, amazing food (get the breakfast pizza!), and if you’re a dog person, they’re everywhere ?

After you get some goodies there, you can walk north to the Lincoln Park Zoo. There’s a bridge near the south entrance that has a great view of the skyline (pictured above), and the zoo itself is completely free! Wander in and out as you please!

6. Shop on Armitage Avenue

You’ll hear a lot about the shopping on the Magnificent Mile and Oak Street, and those are exactly what some people want! If you live somewhere that doesn’t have Topshop and H&M, the Mag Mile will be a dream for you! And if you’re looking to drop some serious cash on designers like Hermes and Prada, head straight to Oak St.

That being said, if you’d rather shop some unique boutiques and grab something to eat somewhere that locals like to go, head to Armitage Ave. You can read all about my favorite shops in Chicago here, or just stroll up and down the street and then grab an afternoon cocktail at Summer House Santa Monica!

7. Go to Second City

There are a lot of places to see improv here in Chicago, the reality is, there’s a reason why so many SNL cast members are Second City alums. It has one of the most prestigious training programs in the country, and their shows and talent are consistently hysterical. It’s also such a blast to look at all of the photos they have hung on the walls – old pictures of Tina Fey, Steve Carrell, Amy Poehler and so many more. The gang is ALL there!

If you’re not into comedy, I also highly recommend seeing a show at the Chicago Shakespeare Theatrer on Navy Pier. I didn’t include Navy Pier itself isn’t on this list because it’s a little crazy during the day, but going for a show at night is a different story. Chicago Shakes puts on incredible productions, plus you catch a glimpse of the skyline at sunset and see the Ferris Wheel all lit up at night. (PS. Adam and I saw Macbeth there last week and it was incredible!)

8 Go to a Celebrity Chef ‘s Restaurant

If you nerd out about celebrity chefs, treat yourself to a meal at one of their restaurants before or after seeing a show! We’ve got three restaurants by Stephanie Izard (Girl & the Goat, Little Goat, Duck Duck Goat), four by Fabio Viviani (Siena Tavern and Bar Siena are my faves), five by Rick Bayless (I’ve been to Frontera Grill and Xoco), and if you watched the most recent season of Top Chef, say hi to Joe Flamm at Spiaggia! Oh, and I know they aren’t celebrity chefs, but if you love the Rancic’s, RPM Italian and RPM Steak are pretty awesome.

9. See a Cubs Game at Wrigley Field

I know I could just say “see any sporting event” – but as a Cubs fan, I have to send you to Wrigley Field, right?! You can read all about my love for this historic ballpark in this post and this post, and those don’t even mention the major upgrades! There is now a beautiful hotel across the street with great restaurants, and a pretty little grassy area just outside the stadium. Get some tacos at Big Star, sip a beer in the bleachers, stock up on cute Chicago Cubs gear, and sing along during the 7th inning stretch. You won’t regret it!

10. Get an Instagram at Restoration Hardware and/or Soho House

Both of these places have the most GORGEOUS decor, so if you love a good instagrammable interior, add one (or both!) of these places to your list! Soho House is a staple here in Chicago, with cozy couches and beautiful big windows. But if you want a little bit of history, our Restoration Hardware is inside of the Three Arts Club of Chicago, which was originally built in 1914!

This newly rehabbed multi floor gallery is an incredible mix of old and new, with the original courtyard re-imagined into the most stunning glass cafe. Once you get a seat by the fountain and and start sipping a cup of coffee or glass of wine, you’ll already be dreaming about when you can come back next!

11. Go to the Art Institute (or one of our other museums!)

*image via

We are so lucky to have amazing museums here in Chicago – The Field Museum, The Museum of Science and Industry, The Shedd Aquarium, The Planetarium, The Art Institute… we’ve got it all! While the view from The Planetarium is absolutely breathtaking, if you can only go to one museum, I usually suggest The Art Institute. Not only is the building itself absolutely stunning, but it features some really incredible one of a kind pieces.

My favorite? A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat. Even if you’re not an art aficionado, you’ll recognize this piece from Ferris Bueller’s Day Off (pictured above!). And if you’e a musical theatre nerd like me, you’ll have Sunday in the Park with George music in your head for the rest of the day. (Helloooo George, where did you goooo Goerge?)

12. Go to North Avenue Beach

And last but not least, North Avenue Beach! You’ve seen me post this view many many times. It has a special place in my heart because I’ve lived close to this view for so many years now… but I swear it’s just as beautiful in person as I say it is! You’ll see people running and biking along the lakefront trail, people tanning and playing volleyball on the beach, and plenty just enjoying the warm weather. It’s active and peaceful at the same time, and I absolutely love it.

Pro Tip: Navy Pier has a firework show at 10:15pm every Saturday over the summer and you can watch it from the grassy area just south of North Avenue Beach. One of my favorite weekend activities over the summer!

Did I leave out any of your favorites?!

if you’re local, where do you like to take your out of town guests? And if you are planning a visit, I’d love to know if there is anything else you’ve been wanting to do/see while you’re here! Or if you just visited, what was your favorite part? There’s so much to do in the city, I like to make sure I’ve done it all myself, too!

PS. You might also like…

Best Chicago Patios
Best Shops in Chicago
The Best Outdoor Concerts in Chicago this Summer
My 8 Favorite Coffee Shops in Chicago
Best Healthy Spots in Chicago
Best Chicago Date Night Restaurants

SaveSave