Last week my family and I truly discovered Chicago. My husband and I usually go every fall to this beautiful city for business but this is the first time we took our two oldest kids and enjoyed Chicago for pleasure.
This post is a family guide to discovering Chicago, we live in MN and it can be a daunting task, let alone expensive if you don’t know how to maneuver your way around the city. In this post, I share my tips and experience for a family staycation at one of the most exciting cities in the U.S.
Our Trip
We decided on a 4 day 3-night stay, we weren’t taking our baby so we had to make the most of it. We stayed at the Embassy Suites By Hilton Chicago Downtown Magnificent Mile (Note there are two locations in Chicago, this one is closest to Navy Pier). We chose this hotel for several reasons:
- The location
- Free wifi
- Free breakfast
- Pool
- 2 room suite ( 2 double beds + pull-out sofa bed)
- Free cocktails every evening
We also decided not to drive, we didn’t want to deal with the hassle of parking in the city, the cost and the delay in case there was construction. This was one of the best decisions we made because of the 4th of July weekend. π So we flew to Chicago via Spirit Airlines (flight time 1hr 15min tops both ways).
We purchased the Chicago CityPASS (another great decision) before hand so we could bypass all the lines to the attractions and save on admission. We wanted to visit 5 attractions while in Chicago and it would have cost us over $200 per person without CityPASS. Here’s a list of attractions you can use CityPASS for:
- Shedd Aquarium
- Skydeck Chicago
- The Field Museum
- Museum of Science and IndustryΒ ORΒ 360 CHICAGOΒ
- Adler PlanetariumΒ ORΒ Art Institute of Chicago
Note – you can only choose one of the last two listed but you get a booklet with coupons to the others as well. We saved over 50% using the Chicago CityPASS
In addition toΒ visiting the attractions above, we also enjoyed dinner at 3 amazing restaurants each night.
- Giordano’s (famous for their deep dish pizza)
- Indian Garden Restaurant (I’m a sucker for Indian food, the cocktails were amazing too)
- Maggiano’s Little Italy (Not the best Italian I’ve had but the service was phenomenal)
Our last night in Chicago was actually my birthday, my hubby surprised me with a Sunset Cruise on Lake Michigan by Wendella Boats & Cruises. This was the cherry on top of an already amazing trip.
Plan Your Trip
To save time and money, you need to plan ahead. Decide how many days/nights you’ll be staying, your budget, and what you can and can’t do if you’re taking kids. We planned on going for 4 days and 3 nights and since we were taking our kids I wanted them to experience as much as possible each day. We planned for 2 attractions each day and dinner. Map out your attractions and distance so you’re not going across the city to your second destination.
Travel Tips
- Get a hotel that offers Free Breakfast (This saves you time and money)
- Get a hotel that has a pool (check pool hours and restrictions if taking kids)
- Book directly with the hotel (You get better rooms and service)
- Take a cab/taxi (This saves you time and money) Think about how much parking in the city costs + time trying to find parking, especially in the summer months when there are tons of road constructions.
- Get a CityPASS (This saves you time and money) don’t spend your vacation waiting in line, get fast lane or VIP entry with Chicago CityPASS and save $
If you have additional tips for discovering Chicago Please go ahead and share with my readers below.
UPDATED POST: THIS POST ORIGINALLY APPEARED ON MY FIRST BLOG FAITHFULLY ME, WHICH I HAVE REINVENTED INTO LIFE WITH KAMI.
This seems like a great hotel! I love that they have free wifi. Much needed after a long day of sightseeing, then wanting to add photos on social media!
I needed to see this! I am currently pitching to hotels in Chicago and this was one of the ones on my list! Thanks for this!
I’m always up for visiting museums with the kids. There looks like a lot of fun things to do in Chicago
We had the opportunity to visit Chicago as a family a few years ago. We absolutely fell in love with the sights and with its people.
The very first trip hubby and I took together was to Chicago!!!! Such a lovely city!!!!
I’ve never been to Chicago but it’s on the bucket list. I think a Chicago City Pass is a great way to see the city.
I love LOVE Chicago. I have never been able to take my family, I need to!
What a wonderful post on your family’s adventure in Chicago! The windy city is definitely one of my favorite places to visit. Will plan a trip there in the summer with my fam too! Thanks for sharing!
Even though I have family in Chicago, it has been over a decade since I’ve visited. I definitely need to visit again someday soon, though.
I love here and there are definitely some great places to go and things to do. You hit up a few of the favs!
Thank you Rachel!
It’s always nice to go to a new place with the kids! It’s fun to explore and it’s really perfect for quality time. I agree with your tips, staying in a hotel with free breakfast is easier because you don’t have to go around looking for food anymore. The cityPASS sounds like a great way to get around and to learn more about Chicago!
Amanda for sure, the kids learned so much while we were there and yes the free breakfast definitely made our stay easier especially in a city.
I love Chicago. It’s a beautiful city with amazing food. I used to live there and still go back to visit. One of my favorite tours is the Architectural Boat Tour. It is so interesting and a fun way to spend a couple of hours touring the rich history of Chicago buildings.
Thanks for sharing, I will definitely check out the Architectural Boat Tour next time I’m there!
Looks like you had a great time! I have been dying to visit Chicago! Thank you for sharing all of your tips.
Teresa, definitely you should plan a trip! It’s so beautiful.
You husband is so sweet! I would love a sunset cruise! I am only a train ride away from Chicago, as I live in the suburbs. I should start leaving my husband hints!!
Awe, thanks so much Rachel! The sunset cruise was definitely the highlight of the day! Start leaving those hints π
I have never been to Chicago but I’ve always heard it’s a great city! It’s definitely on my list of places that I’d like to visit!
Lisa, it certainly is a great city. I hope my guide helped you π
What a lovely city. i have always wanted to visit and i hope to one day. I see a lot of things i would enjoy.
Rebecca, I hope you do too. It’s so beautiful there π
Awesome!
Thank you for sharing.
You are most welcome, thanks for stopping by xoxo