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It can be tough choosing the best extended family vacation spots. I am happy to go anywhere and experience almost anything but when you’re factoring in multiple generations and then a girls only trip, there are a few more things to think about! My grandmother, aunt, and cousin live in Kenosha, WI which isn’t too far of a drive from Chicago, I’m from Phoenix, AZ and my mom is from San Clemente, CA so we decided to make it a multi-gen girls’ week and all come together to stay in Chicago, IL where there really is SO much to do for a wide range of ages.

Multigenerational family vacation in Chicago, IL

WHERE TO STAY IN CHICAGO

There are many little neighborhoods and locations to stay when traveling to Chicago. It definitely helps to know what you might need as a group. For example, will you need wheelchair accessibility? Will you need something with an elevator? Do you want a living room or space to relax in as a group? Will you need cribs or baby amenities? Making a list before you start searching will help narrow your possibilities.

Homeaway condo for multigenerational family vacation in Chicago, IL

Another thing to think about is where will you want to explore the most or where will you be spending most of your time? Downtown Chicago in “The Loop” is a very popular place to visit and has a TON for families and multiple generations to do. Will you want to stay in The Loop or will you be ok commuting a small distance? Do you need a parking space? Parking is limited in Chicago and many places don’t have a parking space or charge a good amount for parking each night.

Homeaway condo for multigenerational family vacation in Chicago, IL

After some searching my Mom and I decided on the Wicker Park / Bucktown neighborhood in Chicago and I’m so glad we did! It is a charming neighborhood area with LOTS of families. We rented this condo from Homeaway and really enjoyed our stay! It was about 1/2 mile from an L station that was super convenient to take right into (and around) The Loop.

Homeaway condo for multigenerational family vacation in Chicago, IL Homeaway condo for multigenerational family vacation in Chicago, IL Homeaway condo for multigenerational family vacation in Chicago, IL

It had 3 bedrooms, 2 bathrooms, and the cutest little living room area that was perfect for late night games all together and a relaxing morning. Had we been in separate hotel rooms we wouldn’t have been able to spend as much time relaxing, talking, and being together as a group.

Homeaway condo for multigenerational family vacation in Chicago, ILHomeaway condo for multigenerational family vacation in Chicago, IL

A home or condo is my favorite way to do multi-gen travel because you CAN spend that down time together and it becomes easier to plan different things throughout the day based on interests and abilities. This way you’re not forced to find something to do together as a big group every day since you know you’ll have time together for breakfasts/dinner at least.

WHAT TO DO IN CHICAGO ON A MULTIGENERATIONAL FAMILY VACATION

There is SO much to do in Chicago so you’ll definitely have many options when planning. Take advantage of sites like TripAdvisor and Yelp to get reviews of parks, events, museums, tours etc.

Have a plan or make lists of things that different members of the family will enjoy or can participate in. Museums, parks, or spaces like Navy Pier are great because older family members can find a nice place to sit and rest while others explore more. Here are just some options:

This is by far not a complete list but should get you started! Chicago is a city that you can plan a ton ahead of time or just go with the flow and still find plenty to do.

WHERE TO EAT IN CHICAGO

Food might just be the most difficult thing to decide on when traveling with multiple generations. Especially if you through food allergies or intolerances into the mix! If you’re staying at a condo or suite with a kitchen you can shop when you get in and have easy breakfasts at “home”. You can even pack lunches if you want to save some money or just make it a day in the park.

I am a foodie, but a gluten free foodie so that limits my choices a bit. One thing I’ve learned from traveling is not to trust any one app and to just ASK. So while there are so many places to eat in Chicago here’s where we ended up on this trip:

  • Small Cheval – this was a short walk from our HomeAway rental and has AMAZING burgers & fries. I had mine without a but and the flavor was excellent. They have a stripped down, easy menu of burgers, fries, and drinks. I loved the atmosphere of the patio and loved seeing neighborhood families and friends meet up here for dinner.Small Cheval restaurant visited while on a multigenerational family vacation in Chicago, IL
  • U.B. Dogs – a Chicago Dog was a must on our trip but me being gluten free makes it a little more difficult. I decided to go to U.B. Dogs off of a recommendation and it was just what I was looking for. The only thing that would have made it better would have been if I brought a gf bun in my purse lol! Even when they were busy the staff was super nice, didn’t make me feel bad for ordering no bun and made us feel like they truly were grateful for our business (even though they clearly didn’t need it). The Chicago Dog was great, fries good and it was the perfect location to stop at while we were exploring around The Loop.Where we ate on a multigenerational family vacation in Chicago, IL
  • Takito Kitchen – this was my choice for dinner one night and it was excellent (this is coming from a Phoenix girl who is picky about her tacos). The food was fresh, inventive, and flavorful while the staff (and owner) were all great. They have a bar in the West Loop as well. I love that they make tortillas specific to their different tacos and my mom loved their chips. Oh and their entire menu is naturally gluten free!Where we ate on a multigenerational family vacation in Chicago, IL
  • Seven Lions – Seven Lions was a restaurant we happened upon during happy hour before our river cruise and it was just meant to be. I loved the ambiance, they have a great happy hour, the drinks were excellent, AND they had a gluten free menu. This is a place I would frequent for sure if I lived in town.Multigenerational family vacation in Chicago, IL Multigenerational family vacation in Chicago, IL

The one thing we did not have while in town was pizza. Before I was gluten free I did visit Gino’s East a few times so I do know what I’m missing, but will take any gluten free suggestions for next time!

CHICAGO ARCHITECTURE FOUNDATION RIVER CRUISE

If you’ve never heard of it the Chicago Architecture Foundation River Cruise is the top tour in Chicago and one of the top ten tours in the U.S. according to TripAdvisor users. They were kind enough to sponsor a tour so I could experience it first hand while I was in town and it did not disappoint.

The Chicago Architecture Foundation River Cruise during a Multigenerational family vacation in Chicago, IL

The tours are led by volunteers (called docents) who obviously love what they do. We did the twilight river cruise and the time of day was absolutely PERFECT. They’ll tell you about buildings and the history of architecture of Chicago during the 90 minute cruise. I found it completely fascinating and can’t wait to come back with all my boys. Even as teens, I think they’d find it super interesting and love the 90 minutes of relaxation during the sunset.

The Chicago Architecture Foundation River Cruise during a Multigenerational family vacation in Chicago, IL The Chicago Architecture Foundation River Cruise during a Multigenerational family vacation in Chicago, IL

I highly recommend looking into this river cruise if you’re traveling with multiple generations! The Chicago Architecture Foundation has many other tours as well so I’ll be checking out more for sure. Here is a full photo tour of our trip:

Author

Allison Waken is the founder, writer, photographer, and content creator of All for the Memories and All for the Boys.

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