Weekend Guide to Chicago

Chicago River Michael and I spent Labor Day weekend in Chicago.  It was my first time to visit the Windy City!  We hopped on a flight after work on Friday from DC to Chicago.


Our first stop when we arrived late Friday night was Lou Malnati’s.  We couldn’t visit Chicago and not have deep dish pizza!  It was delicious.

Lou Malnati's


We started our Saturday morning at Intelligentsia coffee shop.  I’m a sucker for a good coffee spot, and this one did not disappoint!  The staff was super friendly and the coffee and scones were amazing!

Intelligentsia Intelligentsia Intelligentsia

Next on our list was the bean!  The “bean” is actually called Cloud Gate and is located in Millennium Park.  The park itself is a great spot to walk around.  It’s located in the heart of the city and has an outdoor amphitheater, other art and sculptures, and great views of the city’s famed architecture.

Outfit Details: Dress | Bag

The Bean Wind City

Next on our list was the Willis Tower’s Skydeck.  The Willis Tower is the tallest building in the Western Hemisphere and is home to the Skydeck on it’s 103rd floor, which has a glass viewing platform, the Ledge, where you feel like you are walking on air.  The Skydeck provides 360 degree views of the city.  It was a bit overcast when we visited, but the views were still outstanding.

Willis Tower

The Ledge.  Truth be told, it was a bit nerve racking stepping out onto the glass platform.

Willis Tower

After our morning full of site seeing, we decided to take a little break and head over to Doc B’s Fresh Kitchen for lunch.  I would highly recommend the Napa burger.  There is something about the avocado, watercress, dijon honey mustard combo that makes this burger out of this world.  It was SO good.

Doc B's Doc B's

After lunch we decided to walk off our burgers by strolling over to Navy Pier.  We walked through the shops and glanced up at the ferris wheel but decided to take in the view of the city from the ground.

View from Navy Pier

We capped off the afternoon by heading back into downtown along the river and stopping at City Winery.  City Winery sits right along the river and has an expansive patio so that you can take in the views while enjoying one of their wines that is produced onsite at their fully functioning winery.  This is a great spot to enjoy an afternoon drink by the water and watch all of the boats passing through the river.

City Winery City Winery Wendella Boat Tour

Saturday evening we decided to do an architectural boat tour.  This was my favorite thing that we did all weekend!  There are several different companies that offer these types of tours up and down the river, but we went with Wendella Boat Tours.  Our tour took us up and down the river as our guide pointed out each building and the history behind it.  We decided to do the tour that included going out onto Lake Michigan, which I would highly recommend.  Going through the process of exiting through the lock and dam to get into the lake was worth adding this part onto the tour.  It’s a pretty cool process to watch.  And the guide explains the entire process as it’s happening.  If you decide to take a boat tour, I would definitely choose a time around sunset.  We went on the 6:00 tour and ended up having the most amazing sunset view of the city.

We ended the night with a late dinner at The Purple Pig upon a friend’s recommendation, and it was wonderful.  I would recommend sitting at the bar that overlooks the kitchen.  I was in awe of the chefs in the kitchen and how quickly and efficiently they were cranking out delicious plates.

Wendella Boat Tour Wendell Boat Tour Wendell Boat Tour


Sunday morning we had the best brunch at Beatrix before heading to the Magnificent Mile to check out the shopping scene.  After popping in a few stores, we decided to make our way to Wrigleyville since the Cubs were in town.  We didn’t actually have a chance to go into the stadium because the game was sold out, but we walked around and took in everything that Wrigleyville had to offer!

I don’t have any snaps from dinner that night, but we went to Big Star in Wicker Park for margs and tacos and it was SO good!  If you’re in the mood for guac and fresh tacos with a fun atmosphere, this is your place!

Wrigleyville Wrigley Field

On our last morning, where did we end up … Intelligentsia, again.  I’m a big fan.  This was one of the best lattes I’ve had in quite a while!

Intelligentsia Intelligetsia

It was Labor Day weekend after all, so we had to at least make a pitstop at the beach.  We went to Oak Street beach, which is in a great location.  It’s pretty bizarre to be on the sand with skyscrapers in the background.  One thing about the city that I was constantly amazed by is the color of the river water and Lake Michigan.  The river through downtown is a stunning turquoise color and Lake Michigan is crystal blue.  They don’t make rivers and lakes like that in Louisiana.  😉

Oak Street Beach Oak Street Beach Oak Street Beach

After the beach, we had to walk in Eataly.  I could spend hours in there looking at all of the meats, cheeses, and olive oils.  We snagged a pizza for lunch.  It was delicious, of course.

Eataly Eataly

Our last stop of the trip was the Terrace at the Trump Hotel.  The views of the city from the Terrace are amazing.  You get an entire view of the river, the stunning buildings that line it, and a great view of Lake Michigan. *Editor’s note – This trip was taken in 2015, prior to Trump running for and becoming president.  That was my first and last Trump hotel to visit.  🙂

And we snagged some famous Garrett’s Popcorn at the last minute thanks to a friend’s recommendation!

Trump Tower Garrett's Popcorn

We had the best time in Chicago and can’t wait to go back again!  We’ll be waiting until after the winter months come and go though.  🙂  If you have any questions about any of the restaurants or places that we visited, let me know!  Also, we used this Chicago City Guide from Liz at Sequins & Stripes, a blogger that I love who lives in Chicago, to guide us through the restaurant scene.  She definitely didn’t lead us astray!