I spend a lot of time in this city, and I've explored a lot of it's corners. These are my top recommendations.
Map
Dining, shopping, cruises, rides, a children's museum, theatre, live music, fireworks, and more.
Navy Pier
Free zoo with tons of special events like adult nights, haunted history tours, christmas lights, and more.
Lincoln Park Zoo
I could spend all day with the dolphins, but there is so much to see here.
Shedd Aquarium
A full day activity with a variety of exhibits for all ages.
Field Museum
Fantastic outdoor music festival in Grant park with a good variety of acts over one summer weekend.
Lollapalooza
So much to do, see, and interact with.
Griffin Museum of Science and Industry
It sounds so cliche, but deep dish really is a Chicago must have and Giordanos is a classic.
Giordano's
Pricey, but some of the most inventive and fun presentations and flavors I've found.
The Aviary
Cruise along the Chicago River and learn about the skyline. Full bar on board.
Chicago River Boat Architecture Tours
Nightly comedy and improv
The Second City
Interactive and bright museum. Great way to spend a few hours.
Color Factory Chicago: Immersive Art Experience for All Ages
Shockingly delicious with a good amount of options.
Nando's PERi-PERi
Pricey cocktails, but worth the incredible views.
The Signature Lounge at the 96th
So many floors of snacks, sips, and cocktails. Crowded, but comfortable overlooking the Magnificent mile.
Starbucks Reserve Roastery
One of the most unforgettable meals in a very iconic hotel
Shanghai Terrace
Weekend afternoon tea for a special splurge
The Lobby
The best market I've been to stateside with a lot of really great German offerings.
Christkindlmarket Chicago
A great downtown great space. Home of “The bean,” or Cloudgate. Tons of free events. Workouts, movies, music, festivals and more.
Millennium Park
Iconic and historic ball park. Home of the Cubs.
Wrigley Field
Venue, lounge and arcade located in the old Morton Salt factory.
The Salt Shed
Experiential museum that is great for the 'Gram
WNDR Museum
Tons of locations, crazy flavors, perfect for hot Chicago summers
Jeni's Splendid Ice Creams
I can't even explain my obsession with this place, but it was love at first site. Casually cool and fantastic cocktails.
MONEYGUN
Set just off Michigan Ave overlooking the Chicago river its a great location, a little quieter than right on the main road. Hit the fitness center for 360 views.
Swissotel Chicago - Luxury Hotel in Chicago - Swissôtel Hotels & ...
Comfortable, reasonably priced hotel with a pool one block off Michigan Ave. Close to the Starbucks reserve. Very walkable with access to tons of restaurants and shopping.
River North Hotel Chicago | AC Hotel Chicago Downtown
Fantastic hotel in a favorite quaint neighborhood. Suites available, spa and fitness center on site. Lap pool available. Turn down service offered.
Waldorf Astoria Chicago Hotel | Official Site
This hotel is in the CENTER of the action. Close to Millenium Park. Five star service, gorgeous property, excellent restaurant.
