April marks four years since we made the move from Southern California to Chicago. And May marks four years since we bought our first home! I honestly can’t believe how fast the time has gone. We love it here! There is SO much to do. We have the best museums and parks at our fingertips. Everything is within walking distance. And the city never feels too big. It’s just right for us!

But of course, one of our favorite things to do is meeting friends for dinner or drinks and just enjoying the company - maybe with a killer view ; ) We’ve spent countless evenings checking out new restaurants. We’ve taken out-of-town visitors to sexy cocktail lounges. We’ve sipped wine at a rooftop bar for date night. We have tried a LOT of places. Four years in the city will do that!

So I decided it was time to put together a list of some of our favorite spots. Not just in our neighborhood (check out My Favorite Lincoln Park Restaurants here), but in Chicago. So when you’re visiting for a weekend - or maybe you already live here and need to try something new - pull this post up and try one of these spots! I guarantee you won’t be disappointed.

Cindy’s Rooftop - Best view and perfect after a day of sight seeing. Situated at the top of the Chicago Athletic Club overlooking Millenium Park.

Avli - Great for a leisurely brunch with kiddos or an afternoon glass of wine.

Untitled Supper Club - A speakeasy with live bands and the occasional burlesque dancer! Make sure to check the schedule to see when the band goes on.

Beatrix - Ideal for girls brunch or dinner. The River North location is situated right by a bunch of other fun bars.

SoHo House - Grab a drink in the impeccably decorated lobby / lounge area. Or sip coffee while you work on your laptop.

Bub City - Best for a fun night out! Live cover bands play country music - be prepared to dance.

City Winery (on the river) - One of my favorite spots in the summer (although, they offer igloos in the colder months). Soak in the river views and watch boats dock while you sip sauv blanc.

3 Arts Club Cafe - Restoration Hardware’s cafe is dreamy. Bring your family or friends here for lunch. Walk around the show room while you wait for your table.

Summer House Santa Monica - Best for group brunch. They have a Vitamin D room and a rose cart. What more is there to say?

Monteverde - Best modern homemade pasta. Chicago has no shortage of italian joints, but this place feels more modern and the food is unbeatable.

Bar Siena - Great date night spot! I love cozying up here in the winter with some red wine and sharing a few appetizers.

Cafe Ba Ba Reeba! - One of our all time favorite spots to take out-of-town guests. Tapas and sangria are a perfect combination. The menu is extensive and the vibe is up-beat.

Duck Duck Goat - A must try! We came here last year with another couple and ordered almost everything on the menu to share. We walked away wanting more, it was that good!

J Parker - Come here after walking around Lincoln Park Zoo. Great views of the city and the lakefront.

Celeste - Great place to dance the night away! Celeste is the main floor restaurant, but the building also boasts an impressive rooftop garden to sip cocktails until it’s time to hit the 3rd floor disco!

And there you have it - happy travels!