Fly and stay in Chicago, Illinois while also getting to see Wisconsin and Indiana. From the city to national parks to quaint suburban towns, you’ll see it all!! Map is available so you can have it already mapped out for you🤍
Map
Sections
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Hotel/Flight/Car Rental
Saturday
Sunday
Monday
Hotel/Flight/Car Rental
all the boring stuff before the fun stuff you know the deal
This is where we stayed and I could not recommend this hotel and location enough. You will not have to drive/uber anyway. All tourist activities are along the magnificent mile and this hotel is right in the middle of it!
Warwick Allerton - Chicago | 4-Star Hotel in Downtown Chicago
Hate on frontier all you want, but it ALWAYS GETS ME THERE ON TIME OR EARLY 😭🤣
Frontier Airlines: Low Fares Done Right
Alamo was amazing and quick. No hassle at all. They also upgraded us to a car I will never in my lifetime be able to afford so that was fun LOL
Chicago Car Rental - Cheap Rates
Saturday
Wake up early and start the day in Wisconsin to end it back in Chicago!
This is about 1 hour and 30 minutes from Chicago! It’s a beautiful, quaint town to take you away from the bustling city life. The mansions along the Lake are stunning! You can walk along a path that allows you to sightsee these beautiful mansions.
Visit Lake Geneva
This is a great lunch spot with beautiful views of the lake. I do recommend making reservations ahead of time as it can get busy!!!
Oakfire
After a nice morning and afternoon in Wisconsin, come back to hit the city. Whether you decide to bike the riverwalk or find a new bar/restaurant along the river walk, this is a great place to be!
Welcome to the Chicago Riverwalk
Highly recommend biking or walking here at night and during the day. It’s a stunning view during both.
Oak Street Beach
While you’re here you haveeeee to try some deep dish and I recommend this place!!!
Giordano's Pizza
Sunday
Wake up early and start the day in Indiana to end in Chicago.
This is only an hour from Chicago! If you are interested in checking off a national park, this is for you. It truly puts into perspective how massive Lake Michigan is. It doesn’t take incredibly long to explore either.
Indiana Dunes National Park
This is typical of course! You have to go here for the pics.
Cloud Gate
This is where the bean is located but the park itself is beautiful to walk around!
Millennium Park
I truly could not recommend this river cruise enough. It was so beautiful and what I learned about the architecture was so fascinating. Even if you think this wouldn’t interest you, IT WILL.
CAC River Cruise aboard First Lady
This place has some creative and fun icecream you won’t find anywhere else. So creamy and so good’
Jeni's Splendid Ice Creams in Chicago, Il
Monday
Book a flight later in the day and you’ll be able to fit this all in no problem!
There aren’t many Ralph Coffee shops around and after going, I can confidently say, GREAT COFFEE. I am a coffee connoisseur per my tiktok and I don’t think this place is over rated.
Ralph's Coffee
This is a fantastic place to get breakfast after stopping at Ralph’s for coffee!!! There is something for everyone.
Wildberry Pancakes and Cafe
We didn’t tour it, because of time constraints but it was super awesome to see in person!
Wrigley Field
A lot of people may not realize but McDonals has a university called hamburger university where students go to hopefully become CEOs one day. They have an INTERNATIONAL menu!!!! they change it quarterly, but you are able to try a handful of different...