I recently had a travel client reach out to me for help with a family trip to Chicago. They had their dates set and a hotel booked but were overwhelmed with planning the details.
The client had a few absolute must do’s – a Cubs game, an architecture tour and an anniversary celebration dinner, but the rest of the trip was a blank canvas. They would be traveling for 5 days total but had 3 full days in the Windy City.
Here’s the itinerary we created:
Table of Contents
Day 1: Arrive in Chicago
3:00 PM – Arrive at O’Hare International Airport
3:30 PM – I scheduled a private car to take this family to their hotel so they weren’t worried about taxis or Uber pick up locations while traveling with two kids and grandma.
4:15 PM – Check in to their Chicago hotel
6:00 PM – First night dinner. I included a list of restaurants within easy walking distance of their hotel.
7:30 PM – Since Grant Park was easily accessible from the client’s hotel, I offered a walk to Clarence F. Buckingham Memorial Fountain as a gentle first day bit of sightseeing before putting the kids to bed.
Day 2: Architecture and Baseball
9:00 AM – This is going to be a busy day, so I included a list of coffee and breakfast spots close to the client’s hotel.
10:30 AM – Chicago Architecture Center River Cruise aboard Chicago’s First Lady. A river cruise architecture tour is a must do in Chicago and the one that the Chicago Architecture Center runs is the best architecture tour in Chicago.
1:00 PM – We left some time open for a self guided walking tour of Wrigleyville as part of the family’s Chicago baseball afternoon.
3:30 PM – I scheduled a 90 minute Wrigley Field Tour prior to the game they were attending.
7:10 PM – Attend a baseball game at Wrigley Field
Day 3: Field Museum and Navy Pier
8:00 AM – I added some breakfast favorites to their itinerary for this morning.
9:00 AM – The family spent this morning at the Field Museum, an incredible natural history and science museum that is perfect to include in your Chicago itinerary if you are traveling with kids.
1:00 PM – This afternoon was spent at Navy Pier, which the adults probably would have skipped if they were traveling alone, but the kids were very excited to visit the Pier and ride some rides.
7:00 PM – I added some classic Chicago restaurants to the itinerary and also suggested Riverwalk as an optional evening activity.
Day 4: The Bean, Art, and an Anniversary Celebration
Normally I try to schedule a general tour or an orientation tour for the first full day of any itinerary. For this trip, I was grouping activities together by what made sense in real time and working around pre-scheduled activities like the baseball game the client had tickets for as well as museum schedules. So we didn’t land on a day for just some fun city exploration until their last full day in Chicago.
9:00 AM – Sightseeing in the Loop area and Millennium Park, including Cloud Gate, the famous Chicago sculpture affectionately known as “the Bean.” There are some fantastic guided tours available and also some free tours that hit the highlights of the Loop area. I’ll link to some options below.
12:00 PM – Stop for lunch on the way to the Art Institute of Chicago.
1:00 PM – Visit the Art Institute of Chicago.
The Art Institute website has a really cool feature called My Museum Tour that allows you to create your own personalized Art Institute tour of the things you particularly want to see or follow tours that other patrons have created like “Be Like Ferris Bueller” and “This is So Surreal.” Click the link above to explore the My Museum Tour feature.
4:30 PM – This is the start of the Anniversary Celebration I put together for my client. Stop 1 was Skydeck Chicago at Willis Tower (Formerly Sears Tower).
6:00 PM – Stop 2 was dinner at a fine dining restaurant. There are incredible options for fine dining in Chicago, if you are planning a special night out check here for some options.
8:00 PM – And Stop 3 was The Second City, Chicago’s famous improv comedy show for after dinner. A fun alternative to this would be a jazz show at one of Chicago’s many jazz bars.
Day 5: Last Day of the Family Trip to Chicago
8:00 AM – One last breakfast in Chicago.
9:00 AM – Check out early, ask the hotel to store your bags, grab coffee and head to the Lincoln Park Zoo. Admission is always free. Spend a couple of hours and Uber back to your hotel in time to catch your ride to the airport.
2:00 PM – I scheduled another private car to take the family back to the airport.
5:30 PM – Depart Chicago
A list of links I included in the itinerary I sent my clients for their family trip to Chicago:
A list of classic Chicago Restaurants
A list of kid friendly restaurants in Chicago
All of the restaurants mentioned in The Bear
Where to get the famous Cheeseburger! Cheeseburger! Cheeseburger! from Saturday Night Live
Complete guide to Chicago’s Riverwalk
Action Tours Self Guided Walking Tours Bundle
Moon Guides free self guided walking tour of The Loop
What to see in one hour at Chicago’s Art Institute
Chicago is a great city for a family trip. There’s so much to do and most of it can easily be tailored to keep the kids interested for days. Plus, if you live in the U.S., it’s in the middle of the country and easily accessible from both coasts. Out itinerary is a great starting point for planning your trip. Don’t forget to always check museum opening and closing dates and times before finalizing your plans!
For more family fun check out our lists of things to do with kids in Los Angeles and Santa Barbara!
Keep reading…
11 Pismo Beach Hotels You Should Consider For Your Next Beach Getaway
Shoulder Season Is the Number 1 Travel Industry Secret You Should Try
12 Day Classic Spain Itinerary: A Journey Through an Incredible Country
Leave a Reply