Chicago: Where to Stay, What to Do, Where to Eat

Chicago, you made a good impression on me. You left me wanting more after my quick weekend trip. If you have never been to the windy city, you are missing out. Go! You won’t be disappointed. I visited in the early fall of 2017, on the weekend of the Open House Chicago.

Open House Chicago is a free event that takes place all throughout the city, put on by The Chicago Architecture Foundation. There were 200+ buildings (skyscrapers, repurposed mansions, opulent theaters, exclusive private clubs, private offices and breathtaking sacred spaces.) that are normally closed are require a ticketed tour to explore. But on this particular weekend, all these incredible architectural achievements are open to the public for free! This is a great way to fall in love with Chicago because you get to learn about her background story and see the most beautiful hidden gems.

Ok, back to why I loved Chicago and why you need to go visit this city…

Chicago has the magic of New York City without the grime. This city has history, polite residents, beaches, and it’s a foodies dream. It’s a beautiful city on a lake with a river that runs through it. It has an impressive city skyline with some of the best mix of architecture I have ever seen. It’s a stunning hustle and bustle city wearing a peaceful weighted blanket of civility sprinkled with humbleness. (You know I was captain of the analogy team in high school, right?)

Where to Stay

Ok, so you are convinced and planning a visit to the Windy City. Where do you stay? I think the most central location was where I stayed just west of the Navy Pier along the river. There are so many attraction south and north of the river. If you stay in the middle, everything will be within walking distance. And this city is a great walkable city. You don’t need a car! Especially because parking is SO EXPENSIVE. Most hotels charge $50-$70 a day to valet park!

I stayed in the Swissotel, which I highly recommend. It’s a triangular building which gives you views of the city and Lake Michigan. I recommend getting a city view and a corner room. You will have 3 giant windows with a corner view of the city. You can wake up to the sun rising up between the high-rises and go to sleep with the skyline as your nightlight. It’s was so romantic. Who needs a TV in their room with these views!

Staying anywhere on the river will put you in a central location. There is a mix of hotels and apartment building. So you have a wide selection of hotels and Airbnb’s in the best areas. This is a livable area and a touristy area, but very safe. I felt safe walking the streets at night and Ubering late (2am).

What to Do

There is so much to do in a big city like Chicago, but let me share with you my highlights.

Navy Pier – Navy Pier is a Chicago Landmark that is celebrated its 100^th birthday this summer. It’s a welcoming attraction that juts out into Lake Michigan offering beautiful views. It’s hard to put into words what exactly Navy Pier is. It is a pier with dozens of towering sailboat masts on either side. It is a carnival with a larger than life Ferris wheel, carousel, rock climbing, photo booths, and swing rides. There is a 6 story glass atrium filled with plants called the “Crystal Gardens”. There are a variety of shops and restaurants, an IMAX theater, a precious children’s museum, the renowned Chicago Shakespeare Theater, your kids can play and splash in the Fountain/Play Splash pad in the summer time! Do not forget all the paid attractions you can do, like the bike rentals, helicopter tours, and Bus tours of the city that leave from the pier! All year around there is public art and open museums scattered throughout the indoor portions of the pier. You will need to spend at least a couple hours to really see it all!
Or you can simply stroll the pier.

Millennium Park – No one can visit Chicago and not visit Millennium Park. This is the “central park” of the second city. Millennium Park is a 25 acre public park located in downtown. It’s a nicely manicured and an Instagramers dream! Everything about this park is eye candy. This is also where “the bean” is located. Its real name is “Cloud Gate”. This is the original name given by the artist. It is regarded as one of the greatest public art pieces in the world. Come see the reflective bean and snap a selfie! Millennium Park houses outdoor concerts in the Pritzker Pavilion. The city also hold festivals every couple of weeks in the park space. When I visited in October, I had just missed the big “World Dumpling Fest”. Doesn’t that sound incredible? During the winter months and for the holidays, Millennium Park sets up a giant ice rink and hangs Christmas decorations all around it.

Magnificent Mile – Magnificent Mile or “Mag Mile” is actually North Michigan Avenue. It’s located north of the River. This is where all the shoppers go. Want to see a 2 story victories secret down the street from a huge multiple story William & Sonoma? It’s a consumers dream over here. But in between the capitalism are tiny parks and churches that look like castles. Walking up and down Mag Mile feels a little bit like 5^th avenue in NY but way cleaner and more beautiful.

*Bonus Story* So, here is an example of how nice the people of Chicago are. It started pouring rain one night with strong winds while we were walking Mag Mile. We huddled under our umbrella and hid under a Tommy Bahama awning to escape the rain till it died down. The employee inside told us, you can come in here and wait the storm out. We came in along with another family and we were all dripping wet. We apologized and the 2 employees assured us it was ok, and they would just clean it up later. They proceeded to ask where we were from and make pleasant conversation. WHAT? This type of kindness was shocking and refreshing.

River Cruise – Don’t miss the chance to see and learn about Chicago architecture while sailing on a boat. This is where you will feel that windy city trait! It gets cold and windy out there on the river and lake! These River cruises run all day but I HIGHLY RECOMMEND booking a cruise around sunset. The views are spectacular as you transition from day to dusk to evening. The leave from the docks located on the River walk, you can purchase tickets online or at the booths in person. The River walk is also a beautiful stroll through the city. It’s very similar to the river walk in San Antonio.

Second City Comedy Club – I love comedy. This comedy club is a fun “must do” for adults.  Second city is a bit legendary for the stars that was come out of the club. Second City was the comedy jumping point for many celebrity comedians like Tina Fey, Steven Colbert, John Belushi, Steve Carell, Chris Farley, Bill Murray, Amy Poehler, the list goes on but you get my point. This is a place that produces comedy gold! They have shows that run throughout the week but the weekend improv is what everyone raves about. We caught a Saturday night show that was half scripted with some improve and a total improve 3^rd act. It was hilarious and one of the best parts of my visit. Everyone could use a laugh.

A Rooftop Bar – Chicago is known for its rooftop bars because they offer incredible views of the buildings and the water views. You can find them everywhere, but my personal favorite was The Terrace. It’s the rooftop bar at the Trump Hotel. Put your politics aside and enjoy these views. When Navy Pier sets off its fireworks, this bar offers one of the best views!

Check out local festivals and events – there’s something every weekend!

I did not visit the Willis Tower, Sky deck, Museum of Science or Aquarium, but I will be going back to Chicago one day. Comment below and tell me your “must sees” in the windy city.

Where to Eat

Breakfast:

Eggys is a trendy little spot on the edge of a park. It’s in a residential area between hotels and Millennium Park. They have classic breakfast items and affordable prices. You will see locals and out of towners enjoying this place. The coffee was so good, almost as good as the service. (Again, the Midwest friendliness)

Cupotel is a tiny French coffee shop that serves breakfast. I dare you to order a cup of coffee and plate of food and not take a picture of it. It’s so cute and French and Instagram worthy! This place seemed off the beaten path and full of locals. I will come back to this place again and again.

Lunch:

Portillos for Chicago Style Hot Dogs. Don’t you dare suggest ketchup belongs on a hotdog in this city. A classic Chicago style hotdog consists of mustard, relish, celery salt, freshly chopped onions, sliced red ripe tomatoes, kosher pickle and sport peppers piled onto a perfectly steamed poppy seed bun. This combo sounds intimidating but it was perfect. It paired perfectly with a homemade strawberry shake! Portillos is a type of quick service diner. The food is quality but inexpensive. (Hot dogs are $3!) The atmosphere is reminiscent of a 1930s ballgame.

Dinner: Pizza!
Everyone knows Chicago is known for its deep dish pizza. But not many know that there are many types of styles of deep dish. Where do you find the best deep dish pizza in Chicago? I’ve got them for you. (Feel free to argue, I’m always looking for new pizza to try out!) My top 2 spots represent the two ways to eat deep dish pizza.

1. Giordano’s.
   This is a famous spot for pizza. There are Giordano’s scattered throughout the city. So I thought it would feel like a chain restaurant and not authentic. It felt a little bit like a chain. We went to a location close to the University of Chicago. This meant there were tons of college students there. Be forewarned that the pizzas take about 45mins-1hr to cook, so order early while you are waiting for a table. Giordanos deep dish pizza is more like a pie. It’s loaded with cheese and has a thick crust. It was delicious, but I personally enjoyed their garlic fries more than the pizza. 
2. Pequods Pizza.
   Pequods was literally the best pizza I’ve ever eaten. Maybe because I waited an hour in 45 degree Chicago weather to get inside and eat it. I love this style of deep dish. The crust was soft but not doughy. The cheese would get burnt around the edges creating a heavenly crown around the crust. The thickness was perfect. You could hold it and eat it or cut it with a fork and knife. Pequods is located outside of the downtown area. We took an Uber there and back. It’s in a more residential area. I felt like a local sitting there eating the best kept secret in Chicago while we all cheered on the Cubs game that was playing. If you are going to eat pizza in Chicago, go to Pequod’s. I’m serious, this is a must.

What to wear

The weather in the Midwest is fairly unpredictable. I went in October where the temperature can range from 75F to 40F. I was comfortable in jeans, a light jacket and a scarf. These boots are the cutest and most comfortable to walk in all day. Check them out HERE. (Sponsored post w promo code).

That was the windy city in a nutshell.
Have you ever been to Chicago?
Share with me you’re highlights
xo