A Weekend in Chicago
After being asked a few times for Chicago recommendations, it was time to sit down and write them out! I am no expert on The Windy City, and there are certainly a million things to there, but I wanted to create a quick guide for when you have a free weekend in Chicago.
When To Go
Winters can be brutal in the midwest, so consider that before driving or flying. In Summer, you’ll find glorious weather and plenty of options available. Spring & Fall are less touristy times to visit but be prepared for rain and wind in Spring (it’s the Windy City!) and the legendary Chicago Marathon in the fall.
Why Chicago?
A three-day trip allows you time to hit the major sites, try some deep-dish pizza, and get a taste of where you’d like to explore more. As mentioned, there are endless options for entertainment and food.
Your Weekend Awaits…
Day One:
This afternoon, you’ll arrive in Chicago. Depending on your location, it is an easy drive or flight to one of the two larger airports: O'Hare or Midway International Airport.
Activities: Spend the afternoon wandering the famous Millennium Park, home to the famous Cloud Gate sculpture installed in 2006, aka The Bean. Other sites to take advantage of in the park include Crown Fountain, Boeing Galleries, Millennium Monument at Wrigley Square, BP Bridge, and Lurie Garden. In the summers, you’ll find plenty to do at Jay Pritzker Pavilion and an ice skating rink for the whole family in the winter. From there, walk the famous Magnificent Mile, which hosts upscale shops and excellent restaurants, or head to The Sky Deck for an afternoon viewing of the city from above.
Food: Lou Malnati's Pizzeria, Nutella Cafe, Starbucks Reserve- these three are touristy but oh-so-fun!
Day Two:
Today is a full day exploring the Windy City, so head out to Navy Pier for a stunning view of the city skyline. There are River Cruises, Cinema Rooftops, The Art Institute of Chicago, and exciting museums like The Museum of Ice Cream and The Color Factory. With so many options, today is where I encourage you to dive deeper into one of your interests.
Food: Solita Tacos & Margaritas, Duck Duck Goat, and end the night with a nightcap at a Speakeasy- Chicago has a few hidden; can you find one?
Day Three:
Enjoy a lazy Sunday strolling through the Lincoln Park district of Chicago. Here you will find one of the country's oldest (and last free admission) zoos. They host over 200 animals from around the globe featuring African Lions and American Black bears, to name a few. If zoos aren’t your thing, you’ll find the famous North Ave Beach for a stunning view of Lake Michigan or plenty of shopping nearby.
Food: 2d Restaurant Chicago- Mochi Donuts and Fried Chicken, Athenian Room, The Chicago Diner (further north but meat-free).
Where To Stay:
Four Seasons Hotel Chicago
Pendry Chicago
Park Hyatt Chicago
When booking any of these with me, you'll receive these additional perks:
Upgrade on arrival, subject to availability
Daily Continental breakfast for two guests per bedroom
$100 USD Hotel credit to be utilized during stay (not combinable, not valid on room rate, excludes parking and dry cleaning, no cash value if not redeemed in full)
Early check-in/late check-out, subject to availability
Complimentary Wi-Fi
Tip: If you are not staying directly downtown, I advise you to take the subway, bus, or Uber to your destination to avoid the massive highway backups.
I hope you have found this quick and easy guide to a weekend in Chicago helpful! If you have any recommendations, comment below.
Happy Travels, Hannah
P.S. If you are ready, head to the Book Now section for a 1:1 consultation about your next trip!
