Chicago happens to be the 3rd largest city in the United States. Did you know that?! I didn't.... until last year. even though I've been to the Windy City quite a few times in my life. The first time our family visited, I was 10 and obsessed with seeing the new American Girl Place. We visited the classic museums and the Navy Pier (of course!), and I'm sure rode the Loop and ate some deep-dish pizza along the way. However, not too much of that vacation stuck with me though the years. 

Post childhood, I didn't visit again until high school--and we only stayed in the suburbs for quick weekend trips. My younger sister Clarissa decided to attend a university in Chicago, so that and a spring break service trip have led me in to the city a handful of times in the past 5 years. After 3 full days in the city, I wanted to share some of my favorite things I've done in Chicago... so far! ;) More to come, I hope!

Chicago skyline downtown activities near Milenium Park 

Where should I stay in Chicago? 
When traveling to Chicago, we've stayed at a variety of places. For this trip, Clarissa and I actually stayed with friends (by far the cheapest option). My host told me local places I could visit for meals, and walking to buy dinner felt so #urban. (More on food later!) If you don't know anyone in the city, or if they aren't able to host, look for a local air bnb. Wicker Park is a super adorable area, with fun shopping and places to eat--plus it's right off the blue line of the "L" so I suggest starting there. Honestly, though, just do some research and pick what works for you! (And, if you need to set up an AirBnb account, you can use this code for $40 off your first booking!


I've found that driving in to the city, finding a parking spot, and combining walking with the L is how I prefer to get around Chicago. If you plan to be there for multiple days, you can buy a 2 or 3 day pass, or get a Ventra card. Ventra cards are available at some CTA (Chicago Transit Authority) stations & at local corner stores (like Walgreens). The nice thing about a ventra card is that you can put an exact amount of money on it, instead of paying $20 for a 3 day pass and only using $15 worth! These CTA passes also work on the bus system.

how to get around in chicago

Other Chicago transportation options
Uber and Lyft are pretty common modes of transport these days, just about anywhere... Chicago included! Uberpool is great if you're wanting to split the fare with other riders. And, as this study found, taking Uber may even be faster! 

uberpool and train in Chicago

What to do in Chicago!
There are an overwhelming amount of options when visiting Chicago. Honestly, I think you'd have to live there to see everything on your list. (I would!) Since Clarissa and I were only visiting for 3 full days days, and most of her time would be catching up wiht college frineds over coffee and meals, our exploration time was limited. 

where to travel (Chicago) when you can't afford to travel to Paris or Europe!  

That said, of the plethora of museum options, the Art Institute was most highly recommended. Our parents dragged us to more art museums than one could count growing up, but they must have done something right! Walking in, I immediately started giggling. The architecture reminded me of Europe and I began having flashbacks to my high school trip to Paris! I could go on for days about how wonderful the three hours we spent there were. 

Pro Tip: Visit on a Thursday--the art institute is open late!

the Art Institute of Chicago 

Where to eat (and drink) in the city

what to eat when traveling to chicago, where to eat in Chicago

If you haven't eaten a Chicago Dog yet, you must! I'm obsessed... the hype is real. Although I didn't this trip, the last two times Chicago-style hot dogs have been mandatory menu items. If you're downtown by the loop, I suggest trying Downtown Dogs or UB Dogs

5411 empanadas in Chicago

Above, sushi from Midori Japanese Restaurant in Albany Park, and Empanadas from 5411 in Southport (soooo good!).

where to eat in Chicago orange french toast

If you happen to be on the Brown Line, or decide to visit Albany Park (one of the most ethically diverse neighborhoods in the world!), you simply have to eat at Tre Kronor. It's a Swedish restaurant right across from North Park University. Their coffee is good, and their orange french toast is AMAZING! I also suggest taking a walk next door to the Swedish Shoppe, or grabbing a meal from one of the many Korean/Japanese/Persian/etc. restaurants. (Basically, you can find anything there, and it'll be good!)

best coffee and restaurants in Chicago

Clarissa has long raved about the lavender ice cream at Jeni's in Chicago. Since I ended up shopping off the Southport stop, Clarissa met me there and we walked to Jeni's. I ended up with the Lavender ice cream, and the blueberry/lemon sorbet (I just love fruit!) and she had Lav with Darkest Chocolate. Honestly, though, you can't go wrong with any flavor there!

best views in the city of chicago

Finally, I heard that Cindy's Rooftop Bar (just across from Millennium Park) was the place to be. And it was! Drinks there are pricy ($15+) so be prepared for that, especially if you plan to stay for dinner too. The view is great, though, and we got to watch the fog roll in while the streetlamps turned on. Pretty magical!

What did I miss? I know that I'll be back in the city eventaully... what places should I plan to eat/see/drink my way through? Leave me a comment if you have a suggestion!