The Perfect Itinerary for 24 Hours in Chicago

Chicago has been on my bucket list for 16 years. A few times I started to plan a trip but it never panned out. So I was super excited when I found out that my family reunion was going to take place near the Windy City. Finally, I was going to see the amazing architecture, visit the exceptional museums, and eat my way from one side of the city to the other. The original plan was for Mom and me to fly to Chicago a few days early, but some last minute schedule changes meant that we could only arrive one day before the reunion. Disappointed but determined to make the best of it, I planned an itinerary to maximize our brief visit. Keep reading to find out how we accomplished our perfect itinerary for 24 hours in Chicago.

Arrival 

We arrived at Chicago Midway International Airport at 1:00 PM Central time. O'Hare is the larger and better-known airport in Chicago, but Midway is the Midwest hub for Southwest Airlines and a bit closer to downtown than O'Hare.

Since we only had 24 hours we started our adventure immediately with a ride on Chicago's iconic subway system, better known as the "L." Traveling from the airport to our downtown hotel on the "L" was super easy. Midway station is a short walk from baggage claim. A one-way fare card cost $3 ($2.25 for the fare, plus $0.75 for the card which is refillable). Midway is the last stop on the Orange line so you won't have to worry about which direction to take the train. The travel time to the hotel was approximately 35 minutes.

Hotel 

Chicago hotels can be expensive. Luckily, Mom found a great hotel at a reasonable price. The Cambria Chicago Loop (32 W. Randolph), located in the Loop, Chicago's official downtown area, was the ideal location for a 24-hour trip. We were able to walk or take a short Lyft ride to all of the attractions on our itinerary. Our room was clean and spacious enough for two people to fit comfortably.

We had about 90 minutes to relax and freshen up before hitting the streets. I spent some of that time visiting a Chicago institution, Garrett Popcorn, which was next door to the Cambria.

Room at Cambria Chicago Loop

Chicago Architecture Foundation River Cruise

We walked a few blocks to the Chicago Riverwalk which was humming with activity in the early evening. The restaurants and bars were filling up for happy hour, while kayakers paddled in the river, occasionally jostled by gentle wakes from cruising luxury yachts. Mom and I headed towards the Michigan Avenue bridge to board Chicago's First Lady for the Chicago Architecture Foundation River Cruise. TripAdvisor called the cruise the best tour in Chicago and a must-do for out-of-town visitors.

After a short wait to board the boat and a longer wait at the bar for mimosas, Mom and I took our seats on the top deck just as the boat pulled away from the dock. In 90 minutes, the volunteer docent from the CAF shared the history of Chicago and pointed out the treasures of the city's acclaimed architecture. The tour was informative, entertaining, and a beautiful introduction to the city. I highly recommend this tour to anyone visiting Chicago for the first time.

Chicago's First Lady

CAF docent leading river cruise

Civic Opera Building

Willis Tower

Frontera Grill

In the early 2000s, I watched a TV show that was hosted by Mexican-cuisine chef Rick Bayless. I told myself that when I visited Chicago, I would eat at his Mexican restaurant, Frontera Grill (445 North Clark Street). It took 16 years but I finally made it.

Frontera is located just on the other side of the Loop, across the Chicago River in the River North neighborhood. It is surrounded by other trendy bars and restaurants, so if Mexican is not your taste, there are lots of other dining options.

I was a bit worried that the meal would not live up to expectations after 16 years. However, everything was terrific and I enjoyed the dining experience. The staff was super friendly and the atmosphere was casual. This is a restaurant that can accommodate someone who wants a quick bite to eat after work and a group celebrating a special occasion.

Frontera Grill

Appetizers

Enchiladas

North Loop and Millennium Park Walking Tour

We woke up early the next morning and grabbed breakfast at a small diner inside the lobby of an office building. At 9:30, we met a group of strangers to take a free walking tour of downtown Chicago and Millennium Park. The tour was organized by Free Tours by Foot. This is a pay-what-you-think-its-worth tour. I have taken walking tours with them in Boston, Washington D.C., and London and have never been disappointed. I highly recommend them if you visit a city where they operate.

Bruce was our tour guide and he shared an encyclopedia's worth of knowledge about the history, art, and culture of Chicago. He also gave loads of advice on things to do after the tour. The tour ended at the Cloud Gate sculpture which was the site I wanted to see most. Unfortunately, my 24 hour Chicago trip was coming to a close, but there was one more thing to do before heading out of town.

Sculpture by Pablo Picasso - Chicken by Harold's

The Cloud Gate "aka The Bean"

Deep Dish Pizza

I grew up in New York so eating deep dish pizza is almost sacrilegious, but after walking the streets of Chicago for 2.5 hours, we were starved and I forgot about my misgivings. We found Lou Malnati's Chicago Deep Dish Pizzeria (various locations in Chicago) and ordered The Malnati Chicago Classic, a delicious pie with sausage and extra cheese. It was excellent. This New Yorker could not find one thing to complain about.

Lou Malnati's Deep Dish Pizza

After lunch, we collected our bags from the Cambria and trekked out to the family reunion. One day in Chicago did not scratch the surface of what there is to see and do. However, the quick glimpse of this chic and captivating metropolis has me dreaming of a return trip very soon.