1. Play, yes play, in Maggie Daley Park
Age is just a number when you’re at Maggie Daley Park. Not only is there 180 degrees of skyline views, but there is an adult friendly juggle gym unlike something you’ve ever seen before. Definitely a good place to stroll, explore and interact with. There are steel slides like the fun slides at carnivals that are fun for any age. One of my favorite parts are the circular bucket swings that are supposedly only supposed to be for ages 5-12 (but trust me it’s fine). The swings are in a relaxing laid back position that leaves you looking up to the memorizing skyline. Maggie Daley park also has an ice skating track as well as rock climbing.
2. Grab a beverage in the Parkside Grille then hit the ice skating rink in Millennium Park.
Whether it’s a beer or a hot chocolate, Parkside grill beneath the infamous Bean is the go-to pit stop before lacing up your skates. Millennium Park’s ice-skating rink provides music to skate to and a fabulous photo opportunity.
3. Take a stroll down Lake Shore Drive and enjoy the million-dollar skyline from the Adler Planetarium.
Located on the most southern part of the north side, just a few steps away from the Shed Aquarium, you will find the Adler Planetarium. The Planetarium jets out over Lake Michigan which puts you in a prime position to look back on the entire skyline with a lakefront view. Walking along the lake is a peaceful time no matter what the weather is like.
4. Rent a Divvy bike and petal past Oak Street Beach and North Ave Beach.
This is more so a summer-time thing since the cold wind is so bitter in the winter but, renting a Divvy bike is an affordable, easy, and fun way to get across the city. Download the Divvy app and pay 9.95 (the standard cost for one uber, lyft, or taxi) to rent a bike for the entire day. There are multiple Divvy bike stations around the city in convenient locations. You can pick up and return your bike at any Divvy station you come across. I recommend riding along the lake front by Oak Street and North Ave for some quality people watching in the summer. Oak Street Beach Food and Drink is a tikki hut restaurant right on the sand but you must be 21+ to dine there.
5. Ride the Centennial Ferris Wheel at Navy Pier.
Because the ferris wheel is enclosed, it is open for riders year-round. For $15 out of state, or $12 in-state, the view of the Lake and of Chicago are priceless. This ferris wheel was recently redone for it's 100th birthday for a more modern look to last 100 years to come. Navy pier also offers many indoor and outdoor restaurants, boat tours, and shopping.
6. Take a bus or Segway tour.
The Big Bus Tours in Chicago are perfect if you don't want to do a lot of walking to take in the sites of the city. With an upper deck that can be covered in the winter, this tour will take you to to some tourist sites where you can hop off the bus, take some pictures and hop back on for more. The Segway tours are more of a physically challenging experience of Chicago (although I've seen grandmas do it). Segway tours go from one end of the lake to the other with stops along the way. Before embarking on the journey, you will be taught how to use the Segway, and get some practice in with your tour guide.
7. Learn interesting facts about Chicago as you wait in line for the Skydeck at Willis Tour.
Tickets for the Skydeck are pricey but, you can double dip your ticket at either Navy Pier or The Art Institute of Chicago. The Skydeck can often be crowded which might actually be one of my favorite parts because at every step of the line it feels like you’re in a museum of Chicago. Not only will you learn historic facts about the city by the time you reach the top, but you will also learn about Chicago celebrities, sports accomplishments, and fascinating statistics. By the time you reach the actual Skydeck (those glass boxes you can step out on and walk on the city), you feel prepared to identify landmarks from 103 floors up.
8. Have a meal in the 95th floor Signature Room of the Hancock Building.
Prepare for your ears to pop on the elevator ride up! When the doors open to expose you to the floor to ceiling windows of skyline, prepare for a gust of wind to blow your hats off (for whatever strange reason). The 9
5th floor is for dining, the 96th floor is the lounge that offers drinks only. I highly suggest going at night time because the city lights are amazing (refer to the cover photo of this article). However, do know that the interior of the restaurant is only lit by candlelight so it is near impossible to get a picture of yourself unless you want to cause a scene with your flash.
9. Try Chicago deep dish pizza.
My personal recommendation is LouMalnatis but Georgios, Giordano’s, and Gino's East are all viable options as well. Chicago-style deep dish is like eating a pizza pie, if you don't love cheese and a crunchy buttered crust then do not come to Chicago. Similar to the Chicago-style hot dog, Chicago-style pizza is a big part of the city's food culture. You have got to try the deep-dish because I can guarantee you can't get it like this in any other state. If you're not a pizza lover, try the infamous Portillos for a hot-dog, italian beef, and their amazing shakes and fries.
10. Attend a free concert or movie showing in the Jay Pritzker Pavilion.
You'd have to plan this ahead of time to make sure a concert or movie is scheduled for the day you visit but this outdoor amphitheater is most always free admission. The architecture of the amphitheater is enough to visually satisfy your needs but a movie or a musician creates a reason to bring a picnic basket and a blanket and enjoy the sights and the sounds!
