36 Hours in Chicago: Solo Travel

I was itching to see some family and friends in the Midwest. I was also itching for a solo travel getaway. I combined the two and scored a cheap direct flight into Chicago.

How could I make the most of my time – maybe some quintessential Chicago stops mixed with a little exercise? Here’s how it went:

After not a lot of research, I made an Airbnb in Old Town base camp for my two nights. Old Town was the perfect location. Close to Lincoln Park for running and bicycling and an easy EL train to most sights.

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Orso’s. This old school, Italian restaurants with the perfect mix of dark wood and outdoor seating was perfect for grabbing a bite. Great Old Town location and good food.

Second City. I’d wanted to check out this comedy club for years and bought my ticket beforehand. There are actually four different theatres/stages, but I felt convinced that “Up” was the funniest place to be that night. She the People was an awesome cast of six women and their comedy, witty, timely and appropriately inappropriate at times.
(Worth noting: I bought a railing seat. Was perfect for me – didn’t feel too crammed, not too close to the people next to me since I was going solo.)

Divvy bikes on the shores of Lake Michigan. I love it when cities have convenient public bike systems. So easy and affordable! I was on my bike by 7:00 a.m., so had a couple hours to explore the lake front.

Rooftop brunch. I connected with a friend who I’d met last year on a hiking tour for brunch at Cynthia’s. An amazing place to take in the city on a cloudless day.
Bonus: my friend has Ben brushing up on her Chicago knowledge to be a city greeter and I learned more on our walk back to the EL about the city than I otherwise would have taken in.

Millennial Park. This is a must (and viewing it from above at Cynthia’s first was plus!). An outdoor concert area that seats 7,000, amazing fountains and sculptures- all on a waterfront backdrop. Makes you want to move there.

Boystown.  Seeking out independent bookstores on any trip is a must. Unabridged book store makes you want to curl up and get to reading. After picking up a new book, I headed to meet a friend at Lago Wine Bar for a glass of wine. We liked the vibe so much we stayed for dinner. Wonderful pasta with great wine pairings. Headed to Sidetracks for an after-dinner cocktail – a great gay bar, featuring all the best sing along videos.

Chicago is such a diverse, interesting city and I can’t wait to go back. Next time, I’ll make a point of getting outside of the downtown loop for some actual hiking.

What surprised me. This is one highly taxed city! Sales tax is 10.25%. I seriously thought Seattle was alone on those double digit taxes. Plus, they have an income tax (which we don’t have in Washington). Plus the interstates are highly tolled. I drove from Old Town to Wisconsin and stopped for four tolls!)

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