Chicago For a Weekend: What You Cannot Miss

I recently went to Chicago for the first time and fell in love! I was only there for a long weekend (4 days) to visit a friend yet was able to cram a fair amount of things into a short-ish period of time.

Normally I wouldn’t write a blog post after such a rushed trip, but I happened to have two of the best local tour guides a gal could ask for so I feel perfectly confident doing this.  I also shared a bunch of the restaurants on my Instagram story which resulted in many “please blog about this!” DMs so here I am. You’re welcome :)

Special thanks to my friend Sarah and also Lily of This Darling World (friend and fellow travel blogger/Instagrammer) for showing me the most beautiful, healthy, delicious spots in Chicago! Head over to Lily’s site when you’re done here if you need more Chicago recs.

So what to do in Chicago for a weekend? Here are all the things you cannot miss!


Chicago For a Weekend: What You Cannot Miss


3 Arts Club Cafe at Restoration Hardware is absolutely beautiful and the food is great, too! It’s definitely popular so you can expect a wait but definitely worth it while you visit Chicago for a weekend.  Put your name in for a table when you first get there.  They’ll text you when your table is ready so you’ll be able to kill time shopping at RH or roaming around the neighborhood while waiting. I had the kale caesar and it was amazing!

The Allis is another gorgeous venue with great drinks and decent food. The vibe is really fun (there’s a dj at the edge of the bar) so it’s the perfect place to start a Friday or Saturday night.  There’s also a ton of other bars and restaurants in the area, making it easy to move onto the next after a few drinks here!

Ema is a mediterranean spot which I love because mediterranean is, for the most part, super healthy and delicious.  The space is also absolutely beautiful (you’re shocked, I’m sure).  We went for brunch but you could definitely come for any meal — it all looks amazing!

Beatrix is in the same family as Ema and also neighbors with it physically. It’s a popular brunch spot, featuring what they call “healthy meets delicious options”.  If that’s not right up my alley, I don’t know what is.

Summer House Santa Monica is a West Coast themed restaurant with a California-inspired menu.  The venue is airy, with plants and string lights hanging from the ceiling washed in natural light.  Very Instagrammable!

Colectivo is not a place you should go out of your way to visit, but I did find myself here numerous times during my visit so I wanted to include it in case it happens to be in your neck of the woods. It has delicious coffee, great food (I got some kind of mediterranean wrap one day and then went back the next to get it again), and if you need a place to get some work done this is the perfect option.  You can even work outside!

The Lakefront Restaurant at Theater at the Lake has an incredible view but not-so-incredible brunch food.  I’m including it anyway because the drinks looked great and I heard it’s the only outdoor restaurant on the lake. Cocktails on the patio are probably a good idea if you are there when the weather is nice! And who knows, maybe lunch and/or dinner has better food options?

Bub City is the place to go if you are a country music fan! There is live music everyday of the week (see the calendar here) plus barbeque and good drinks. 



Rent bikes and see the sights — there are a lot of different ways to get around Chicago but my favorite by far is via Divvy.  It is, as they say on their site, “faster than walking, cheaper than rideshare, and more fun than the train”.  

For $3 per ride of $15 per day you can pick up a bike at one of hundreds of stations around the city, ride wherever you want, and then return your bike to any station (doesn’t need to be the original one) once you are done.  

It’s easy when you want to get from one place to the next but it’s also great for giving yourself a tour! Make sure to ride along the lake — there’s a path just for bikes and the view is unreal.

Take a Chicago River Architecture Tour — my local friend would NOT stop talking about this tour so I decided I would do it on Monday. Then I went to finally book it early Monday morn it was already sold out until late afternoon.  Despite having not actually done this, I feel confident enough recommending it based on her review.  

She said it’s the one thing she does every single time she has someone visiting and, despite having done it numerous times already, she never gets bored of it.  It’s at the top of my list for next trip and I’d suggest it be at the top of yours too!

Check out the Riverwalk — the Riverwalk is a 1.25 mile path along the river, full of fun restaurants, bars and more.  I especially recommend grabbing some rosé at City Winery and people watching along the river. 

Enjoy the city views from some rooftop bars — there are many different rooftop bars in Chicago offering spectacular views. Lily said LondonHouse Chicago is her favorite view in the city which I can confirm based on her photos but not from personal experience (there was an >1 hour wait).  Cindy’s is another highly recommended option and my friend suggested the J. Parker.


And if you happen to be there in June and are a country music fan, make sure to check out LakeShake Festival. It's Chicago's three day country music festival right on the water and with the most amazing lineup! I have been to countless country shows and this was by FAR the best, honestly.



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