Chicago Travel Guide

I had the opportunity to visit Chicago for a week and I crowdsourced from my friends and online blogs a list of things to do in Chicago. Since I still had to work, I primarily ate a lot. I really should rename this blog post to A Chicago Food Guide. Although I was only here for a bit, I really enjoyed the city. It has taken its place as my favorite city in the US (probably because I have not experienced its winters). It reminds me of a clean New York without the stressful hustle and bustle and I love how a river flows through the city. I'm a Cali girl and need to be near water.

I’ve categorized the blog post by Places, Food, and Things To Do. Unfortunately, I did not take as many photos as I wanted to, but I've added some HUJI Cam and instastory photos I took in the post. Hope this helps you plan your trip to Chicago or inspires you to make the trip out there!


I mainly stayed in two regions: Wicker Park and Downtown Chicago (right next to Millenium Park).

Wicker Park was a very hip place to be. Imagine insta-worthy coffee shops, thrift stores, and great bars (and a kava bar). It was a great place to work and hang out with friends.

Downtown Chicago is very touristy, as most downtown areas are. Around the area is all the classic tourist attractions: Cloud Gate (The Bean), Magnificent Mile, and Willis Tower. I recommend going to Cindy's Rooftop bar ($$$) for a drink. You get a great view of Millenium Park. Also, if you don't want to pay the $20 entrance for Willis Tower, you can go to the 96th floor bar in the John Hancock building. The view is incredible and we ended up watching the Fourth of July fireworks there.


Main Dishes

Purple Pig ($$$)
Purple Pig is amazing! They serve large size tapas that are all very well made.  I loved it so much I came here twice during my trip. They change their menus every season, but I recommend getting the bone marrow, crispy pig ears, asparagus rissotto, and pork dishes if they are available. The wine is pretty pricey but they have nice cheese plates that pair well with the drinks. The tapas are pretty salty, so drink lots of water and stay hydrated. There is also usually a line here so I recommend coming at odd hours.

Small Cheval ($$)
This restaurant serves the burgers from the famous Au Cheval, without the fried egg on the burger. It’s great if you want to taste the burger without waiting hours for a spot at the main restaurant. 

Nando’s Peri Peri ($)
This place serves great chicken dishes with varying spice levels. It was a great fast meal that was ultra-filling. I had enough left over for another meal.

Wildberry Pancakes and Café ($)
This is a very popular pancake place that usually has a 2hr + wait time. I recommend putting your name down and wandering around. It is located near the Bean, so this is the perfect opportunity to check out the big tourist spots. I ordered an omelet and their fruit pancake (what they are known for)

Beatrix ($$$)
Great for a nice healthy lunch. I got their mushroom quinoa burger and blueberry basil refresher. They serve coffee and also have wifi. I ended up coming back to just work at the restaurant's coffee bar. 

Lou Malnati's ($)
Deep dish pizza is a must! This place is one of the most famous pizza joints in Chicago. They serve great deep dish pizza with standard toppings. Some joints are take-out only, so make sure to check on Yelp before going!

Eataly ($$)
I loved Eataly in NY and was so happy there was a location in Chicago. This place is essentially a super market that also sells amazing food. Lots of great pasta, food finds. I ended up coming home with bundles of squid ink rissotto, pasta, red chilli pasta, truffle salt, and much more. 

Other restaurant's I was recommended but didn't have time to try: Portillo's for Chicago Hot Dogs, Girl & The Goat


Wormhole Coffee ($$)
This is a great place to work if you are in Wicker Park area. The interior of the shop is filled with 80s video game references, along with interesting drinks (Peanut Butter Koopa Troopa, Honey Bear Latte, etc.)

Ipsento 606 ($$)
This was another great work spot with nice lighting and delicious lattes. They had plenty of outlets and free sparkling cold water. The only downside was that they don't serve food (although it said coming soon on the blackboard). This place is located near Small Cheval.

There was also Intelligentsia (any LA Intelligentsia fans??). Two Zero Three was another coffee shop to work at in the downtown area. I was unsuccessful in finding much near the tourist places aside from Starbucks and Peet's Coffee.


Jeni’s Ice Cream
I believe this place is a chain, but it was definitely a great stop in Wicker Park.

Stan's Donuts
Amazing old fashioned pistachio donuts here. This place is a chain, so there are plenty around Chicago!

Do-rite Donuts
Another donut place in Chicago with similar donuts but much fluffier. 


Apologies for having less content available for this travel guide compared to my other ones. I hope it still helps and let me know down below if you visited any of these places!

x Alice