New Year - New Adventures! Chicago, IL Travel Tips

Although Vancouver may be the cleanest, safest, most beautiful city I've traveled to this year, Chicago takes the cake as my favorite. It's full of personality, unique neighborhoods, great city life, amazing restaurants and fun sports teams to cheer on.



Here's Chicago in four days.

First, when packing for Chicago it's very hard to predict the weather - pack everything and be prepared for anything.

Day 1.

We felt the first day it was really important to get the lay of the land, really see the city and get some bearings. After we checked into our hotel, The Talbott (which we loved and HIGHLY recommend), we 

• Went to an Irish Pub a few blocks from The Talbott
• Took an Architecture Tour on the river
• Ate dinner at Eduardo's Enoteca
• Saw a Second City Improv Comedy Show

If you're not very familiar with Chicago Architecture or architecture in general, I'd recommend reading Devil in the White City. It's a story about a serial killer and famous architect set during the 1893 World Fair in Chicago. It's an interesting story but helps give some context about all the architecture on the river prior to taking the cruise. 

Eduardo's Enoteca was a lovely Italian Restaurant and Wine Bar. I always try to find more local spots and this was definitely a local gem. Four stars on yelp led us here and we were not disappointed - the pizza was delicious! 

Finally, anyone who's a true Saturday Night Live fan has heard of Second City. This comedy club opened in 1959 and has produced many of the SNL greats; John Belushi, Tina Fey, Amy Poheler, Chris Farley and many, many more. After an incredible boat ride, fantastic dinner and insanely funny improv comedy show, I was sold on Chicago as one of the greatest cities in America. 

Day 2.

• We ate brunch at "Eggs-perience"
• Rode Divy bikes around the city - From Navy Pier to the Lake Michigan front, to Lincoln Park and Old Town
• Enjoyed a Sushi Dinner & Bars

Little disclaimer - I'm terrible at bike riding so needless to say I was a little skeptical to ride a bike around this unfamiliar city, but despite my hesitation, it was insanely fun. Divy Bikes is a bike-share system in Chicago where you can purchase an hour pass or a day pass, pick up a bike at any station, ride around then drop it off at any station throughout the city. We spontaneously joined an afternoon bar crawl, stopped when we felt like it, and ended up watching a little college football here and there. 

Day 3:

• Bears Game (or other sporting event) White Sox, Bulls, Cubs
• Lou's Deep Dish
• Pourhouse

A good friend of mine plays football in the NFL and his team was coincidentally playing the Bears when we went to visit. We bought tickets to the game and it was an incredible experience. Chicago fans are loyal and energetic to say the least. Besides getting the experience of going to a sporting event at Solider Field, we were honored to experience some standard Chicago weather - it pouring rain the ENTIRE game after it had been warm and sunny the entire day prior.

For dinner at some point during your trip, Lou's Deep Dish is a must. Although a little more touristy than I would like, you cannot go to Chicago without eating traditional deep dish Chicago pizza. 

At night we wanted to watch the 49ers vs. Seahawks game and stumbled upon the Pourhouse. It was a perfect sports bar with about 100 beers on tap. 

Day 4:

• Walked through Millennium Park
• Visited the Signature Room on 95th at Hancock Tower

The last day we were in Chicago I wanted to see the Bean in Millennium Park and go to the top of the Hancock Tower for one last view. Below is the picture from the Signature Room where we enjoyed a lovely glass of wine and then headed to the airport. 

Thank you Chicago! I was blown away :)

Xo, Chels