Planning Three Fantastic Days in Chicago

Three Days Chicago

My parents and sister came up for a visit over Columbus Day weekend, and we had a fantastic time!  I spent a lot of time online searching for good ideas and options for us to do while they were in town, and I wanted to share those ideas here as a resource for others.  Each item on this list meets the following requirements:  (1) not too expensive, (2) easy access by car, (3) close to parking/car in case of a health emergency, and (4) family friendly, as well as caters in some way to the personal interests of my family.

Because we needed a plan we could play by ear, I put together a lot of options and then chose from those options based on how everyone was feeling and the weather.  We had a few extra hurdles this weekend, as this past Sunday was the Chicago marathon and there were many road closures and lots of extra people in the city.

Planning for Meals

No one has fun when they are hungry all day, so I typically plan days with guests around meals and am sure to include snacks.  Before my family arrived, I made sure to cook/purchase lots of healthy and not-so-healthy snacks, based on what my family likes and what I like.  I made sure to have carrots and hummus for a healthy snack, meatballs, cooked chicken, and nuts for protein, and some homemade and purchased cookies and candy for sweet snacks and desserts.

Feeding five people requires a lot more food (and effort!) than feeding two, so it’s important to take that into consideration when shopping.  I thought I did this well but still ended up running out of eggs before we ran out of mornings!  We planned to eat breakfasts at home and to make at least one dinner at home (so we could watch football), but made sure to have other things on hand in case our plans changed and we needed to stay closer to home.  And, there’s always takeout.

Choosing Restaurants

Instead of making reservations that would put stress on our days to be at certain places at certain times, I made a list of restaurant options that I knew we could go to without making reservations.  Here’s what we had on the list:

  • Deep Dish Pizza (a Chicago must) at Lou Malnati’s
  • Sandwiches from Panazzo’s Italian Sandwiches, a lunch location within walking distance from our apartment and with great Yelp reviews
  • Bongo Room, the current winner on my search for the best brunch locations in Chicago — get cheese on your breakfast potatoes.  Trust me.
  • Pita Heaven, another casual walk-in for lunch that added a little variety to our options
  • Uncle Julio’s Mexican Restaurant, with on-site parking and an easy-to-please menu
  • Chinese Food in Chinatown, since Chinese food is a favorite in my family — we ended up choosing Go 4 Food which was delicious!


There is a lot to see and do in Chicago, but I know my family and I know they’d rather do a few enjoyable things than rush around the city trying to fit too much into each day.  My number-one choice for seeing the city without getting a workout is Shoreline Sightseeing’s Architecture River Cruises.  These cruises are fun, informative, and give you a chance to learn Chicago history and really get to know the major elements of the skyline.  I’ve been on two now and would absolutely go again — each tour guide gives you a different feel for the city.  And if you don’t love architecture, it’s still really fun to be on a boat, and kids love the boat noises, going under bridges, etc.  I think it’s a perfect start to the city.  After the architecture cruise, no matter where you go in the city you’ll see a building you remember from the cruise and feel like you’ve learned a little about the city.

Other easy options for sightseeing include:  the Chicago Tribune Building, which is right along Michigan Avenue’s Magnificent Mile of shopping and has a very interesting construction that includes pieces of famous buildings across the world, the John Hancock Observatory and/or Lounge (locals recommend skipping the typical price of the observation deck and spending that money on a cocktail or espresso in the lounge instead), and a spot along Lake Michigan for beautiful city views.  The two options I chose for shoreline views were Promontory Point, a southern-view that would be better for afternoon photo-taking, and North Avenue Beach, to get a feel for what a Chicago summer would feel like.  We opted for North Avenue Beach and I think my parents enjoyed seeing the waterfront and the shuttered beach house.


Finally, you will absolutely want to stop in Grant Park and/or Millennium Park and see the Bean.  It’s really cool and a great photo-taking opportunity.

Other Activities

While cookie-cutter sightseeing is fun for a while, what really makes a vacation are the fun things you do.  I had hoped to take my parents and sister to see the Best of Second City show on Saturday night, but unfortunately it had sold out before I purchased tickets and the Monday night showing did not fit our scheduling needs.  Try to get tickets if you can, but we’ll be saving that for their next visit.  We made sure to stop over at the Amish Healthy Foods Unique Grocery in the Ukrainian Village, and got delicious unusual flavors of gelato from Black Dog Chicago.  Also on the list but not on our final agenda was a Saturday stop at the Green City Farmer’s Market (can you tell we love looking at weird organic food?) and a visit to the Field Museum or the Shedd Aquarium.  On our last afternoon in the city, a stop at the nearby Horseshoe Casino was a fun break.

Finally, be sure to plan for quiet time/individual downtime.  Everyone needs some time to decompress, and that need can be even greater on vacation.  It’s supposed to be fun, so don’t let planning or getting places ruin the fun of it all.  Play some cards, people watch, read that book that’s been waiting for you, and enjoy your time together.


So, what did I miss?  What are your favorite parts of the city to share with your out-of-town guests? 



  1. Nikki Ringenberg

    This may not fit your taste, but the Nile restaurant in Hyde Park is fabulous! The owner is Palestinian (his brother is a poli sci professor at UTC, which is how I found it) and the food shows it. The Field is one of my favorites!!

  2. Dad

    Actually, your mother might not have been up to it, but she is full of surprises. Your sister LOVES an Egyptian hamburger stand here in H’ville.
    And I think you should forget the federal job thing, and the law degree, and become a tour guide. (just kidding) Because you are REALLY good at it. (not kidding)
    Thanks for a wonderful week.

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