Escape from New York

48 Hours in Chicago

Editor’s Note: This article is part of our series “Escape from New York.”  Series Overview: Flight times are within 2 hours and 30 minutes of New York City.  Spend 48 hours immersing yourself in the culture and feel of the destination city.  Flights can depart at 6am on Saturday and arrive back in New York on Monday morning so you can attend your first meeting of the day.  The first article in this series featured a trip to the Niagara Fall region in western New York.  

My destination this trip was the Windy City.  Flight times come in just under 2 hours but you can budget around 2.5 hours for boarding, taxiing, etc.  Having never been to Chicago, I chose to stay in the ‘Loop’ downtown to have a central location where I could then branch out and explore the city.

Day 1

Chicago River Architectural Boat Tour:  Walk along the river downtown and there are multiple boats providing tours of the river.  This was my first activity after checking into my hotel and it helped orient me to the city.  It also was a great way to learn about the history of Chicago and get some nice photo opportunities.

Portillo's Chicago Style Hot DogChicago Hot Dog: I went to Portillo’s based on the recommendation from the Guide of my boat tour.  It took about 15 minutes to walk there and was a nice way to stretch my legs after sitting for 75 minutes.  I ate two for good measure and definitely believe the hype around Chicago Style Hot Dogs.

Lincoln Park and Lincoln Park Zoo:  The benefit of an early arrival to a city is having all day to explore.  After my delicious hot dog experience, I headed north to Lincoln Park in an Uber.  The ride was quick and only cost around $7.  The added benefit of taking the car was I could ask the driver for any recommendations for things to do in the city.

Lincoln Park Zoo is located in the middle of Lincoln Park and is free to the public.  The park and zoo are a nice place to spent 2 hours during the afternoon.

Lakeview Neighborhood:  Located on the North Side of Chicago this scenic neighborhood is perfect for getting a coffee in a cafe and walking around looking at some of the historic brownstone apartments.

Old Town and Second City:  Second City was the starting place for many famous writers, actors and comedians over the past 50 years.  I decided to end my day with an 8pm improv show and it was one of the highlights of my trip.

Day 2

The Art Institute of Chicago – In case you were wondering, they do have a specific Ferris Bueller’s Day tour (and that is exactly what I did.)  A wonderful museum and I can’t wait to go back.

South Side of Chicago, University of Chicago and Hyde Park –  I spent a few hours in the afternoon exploring the University of Chicago and Hyde Park (past and current residents include author Saul Bellow, boxer Muhammad Ali, President Barack Obama and the list goes on.)  I would suggest renting a Divvy bike to explore the neighborhood.

Deep Dish Pizza – I got my first deep dish pizza at Lou Malnati’s and thought it was a great.   I understand everyone is going to have their own preference and I did consult a few best of lists in advance of my trip.  By all means ask around or consult Thrillist for their list.  I went to the restaurant in the North Side of Chicago so I could then stop by Wrigley Field after.  Note: it takes about 30 minutes to make the pizza and is pretty heavy so be hungry and make sure you have time.

Wrigley Field – One of the country’s oldest ballparks (second only to Boston’s Fenway Park.) was built in 1914. The stadium sits in the middle of a neighborhood and you can feel the history as you walk around this iconic place.  Be sure to check out the stadium seating people built on their apartment buildings to watch games from outside the ballpark.

Over the course of the trip I used a combination of 4 modes of transportation:

Walking – One of the best ways to explore a neighborhood.  Plus if you get tired you can grab a car or hop on a bike.

Divvy bikes – Public commuter bikes (like Citi Bikes in NYC.)  $10 for a 24 hour pass is a good deal and they have locations all over the city.Divvy Bike in Chicago

L Train – Comfortable, clean, affordable and a perfect way to cover a lot of ground in the city.

Uber – If you are done walking or riding bikes for the day, grab an Uber.  I only used the service a few times and averaged around $10 a trip which is reasonable.

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