The Best Ways to Spend a Day in Chicago

Growing up near Milwaukee, I was only, at maximum, a two hour car or train ride away from the Windy City. As an adult committed to both local and overseas travel, I’ve made a conscious effort to get to know America’s third largest city a bit better. Thankfully, over the past few years, I’ve actually been able to make it down for a few day trips, or combine a fun activity while going to get a new working visa for France (see 2013, 2014). In fact, whilst home this summer, I had the chance to meet up with my good college friend and former roommate / sorority sister, Erin (whom has accompanied me on several Chicago trips throughout the years!) Erin now lives in Detroit, Michigan, so it was perfect middle ground for us to spend the day together!


Chicago Theatre

I was able to take the Amtrak train direct from Milwaukee to Chicago (1.5 hours, and the most convenient way to get to Chicago, in my humble opinion). So, low and behold, several ideas for a great day trip (or weekend adventure) in Chicago.

  1. Take a Free Walking Tour: Free Tours by Foot is basically the United States’ version of Sandeman’s New Europe walking tours. The company is based in major US cities (as well as some European ones), including Chicago, NYC, New Orleans, Miami, Boston, and Philly. There are many different tours to choose from and they last about two hours each (I chose to take popular tour of The Loop in Chicago). Free Tours by Foot are tip-based tours. Just reserve a spot online, show up, and pay what you like at the end.

2.  Admire the attractions in Millennium Park: As I learned on my tour, Millennium Park is actually one of Chicago’s newest parks, completed in 1997. Right on the Magnificent Mile (Michigan Avenue), it is bustling with sweeping views of the city, fountains, the famous Bean, and during the winter, an ice skating rink.


20768203_10209737728272347_4217059917323712834_n.jpgMillenium Park, Chicago

3. Hang out at Navy Pier: Erin and I decided to venture out to Navy Pier during this past visit. There is a free botanical garden and some great views of the Chicago Lake Front. We decided to splurge and ride the ferris wheel and take in the breathtaking skyline.

On the Ferris Wheel at Navy Pier, 2017

4. Shop on Michigan Avenue: Known for its gorgeous Christmas decorations during the holiday season, Michigan Avenue has some of the best shopping around (it’s kind of equivalent to New York’s 5th Avenue.) It is also home to some of the most sweeping views of the various skyscrapers in the city. Even if you don’t like to shop, simply site seeing and exploring makes for a fantastic afternoon stroll.

Michigan Avenue Views, August 2017

5. Take the Architectural Boat Cruise: Erin and I did this in 2013, and we LOVED it! I learned so much about the Great Chicago Fire and the current architectural designs of the city. It’s a great and informative tour, and the views are impeccable. You can usually just show up and book on the spot.

Spectacular views from our Architectural Boat Cruise, 2013

6. See a Show!: In 2013, Erin and I combined my visa appointment with ticket to The Book of Mormon— still one of my all-time favorites, by the way! Chicago has some of the best theatre scenes in America. Hamilton and Aladdin are some of the current must-sees.


America’s current obsession: Hamilton!

7. Go to a Museum: In 2009, I organized a day in Chicago for my sister, cousins, and cousins friends to go and see the Harry Potter Exhibition at the Museum of Science and Industry in Chicago. In 2012, Erin and I spent the day at the Shed Aquarium. There are a ton of museums to check out in downtown Chicago. Some other popular choices include the Museum of Contemporary Art, the Field Museum of Natural History, and the Art Institute.


My sister, cousins, my cousin’s two friends, and me in Chicago for the Harry Potter Exhibition, circa 2009


Erin and me, circa 2012- On our way to Shed Aquarium, stuck in the rain!

8. Go on a Bike Tour: My mom and I did a bike tour of Chicago with Bobby’s Bike Hike in 2014, when I came to Chicago to apply for my lectrice visa. It is, to this date, one of the best and most favorite things I have ever done in Chicago. I especially loved biking along the lake front and on the beach.

Bobby’s Bike Hike Tour, 2014

9. Indulge in Deep Dish Pizza: Chicago has a great foodie scene, with popular dishes such as Deep Dish pizza and Chicago-style hot dogs. There are many food / beer tours available if you want to have a more personalized experience.

Other ideas for spending a day in the Windy City include climbing Willis Tower or the John Hancock Observatory (or simply indulging in a drink without paying for the observatory fee on the 96th floor), attending a baseball game, having a picnic on the beach, chilling in one of Chicago’s many parks, such as Grant Park, Hyde Park, and admiring the animals at the Lincoln Park Zoo (which is free!)


Other Essential Information: Here is the price breakdown of my day trip to Chicago this past August 2017:

  • $52- Roundtrip train ticket from MKE to Chicago
  • $10- Day pass for the El train (subway) and the bus tickets
  • $10- Walking tour tip
  • $15- Ferris Wheel ride at Navy Pier
  • $5- Lyft ride
  • $29- Sushi meal
  • $14- Happy Hour cocktails for Erin and me (she paid for our taxi fare)
  • Total: $130 including transportation, $78 without

Disclaimer: I was able to save money by bringing my Starbucks gift card and a packed lunch / snacks for during the day. Erin’s uncle also treated us to a delicious meal at a local Mexican restaurant (a shoutout to you, Steve!) I could have definitely spent less at the sushi restaurant, because I underestimated American portion sizes and wasn’t able to finish everything. I also made a mistake in my directions in regards to at which hotel I was meeting Erin, and ended up twenty minutes in the wrong direction (and therefore resulted in splurging a shared Lyft ride.) I believe taking the train to Chicago from Milwaukee was cheaper than driving, because when you include gas and parking in downtown Chicago, it is quite similar. Finally, I paid for Erin’s happy hour cocktail, and she covered one of our taxi fares across the city.

What is your favorite thing about Chicago?



12 thoughts on “The Best Ways to Spend a Day in Chicago

  1. I looooove Chicago. I lived there for five years before I moved to France but I haven’t been back since because my family is on the west coast. The Museum of Contemporary Art has free entrance on Tuesday and the Art Institute is free on Thursday night (…at least they were in 2012…) and they both have amazing (and weird, in the case of MCA) collections. I love those funny spitting faces in Millennium Park in the summer. It’s also so worth going to check out neighborhoods outside of downtown – so much great food and shopping! It might be ambitious for a day trip depending on what else you have planned, but it’s easy to get to most of them on the El (or bike, like you did 🙂 ) I loved seeing your pictures of my old home – thanks for sharing your tips!

    1. I forgot you lived in Chicago! I’d love to get to know the city on that level… Also Great museum tips !!

      LOL at the WI pride, it can be so obnoxious

  2. I really enjoyed the Architectural Boat Tour when I visited Chicago two summers ago! My dad also recommended the 96th floor of the John Hancock building, but at the time I wasn’t quite 21 (a month or so off!) so wasn’t allowed in and had to pay the entrance fee… minor disadvantage to being born later in the school year! I had a couple of friends in the area who showed me round when I was there (an old school friend who emigrated, and a girl I met on my year abroad as an assistante), but I’d love to go back and explore the city more 🙂

    1. Argh the 21-year-old rule in the US is so annoying! I forget about it now! I feel like every time I go to Chicago I discover something new– the joys of traveling! (Although I’ve still not been up Willis Tower)

      1. It was a wee bit frustrating, but I don’t really drink so it wasn’t too bad. Just annoying for little things like the alternative option for going up the John Hancock building! You should definitely head up there next time you’re in Chicago – the views are stunning 🙂

  3. OH! We also saw a play at Steppenwolf about a swingers group by one of my favorite playwrights, and it was incredibly good! So many great theatres producing work in Chi, aside from the touring Broadway productions: Victory Gardens, Shattered Globe, Chicago Shakes, the list goes on! My Chicago theatre friends say the improv and comedy scene is also phenomenal!

  4. My sister, cousin, and one of my best friends have all lived in Chicago and I’ve wanted to go visit for ages, but obviously I’ve been in France…. now that I’m back, they’ve all moved to New York!! Not complaining, because NYC is way easier (and cheaper!) for me to get to from DC, but I’m bummed to have lost that free lodging and tour guide service :P.

    The one time I did go when my sister first moved, I loved the architectural boat tour and the Art Institute! We also toured FLW’s Robie house which was fascinating and visited U of Chicago (where my sister was about to become a student) and Hyde Park which were stunning. If I make it back, I’d love to spend more time on the waterfront!

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