Chicago…it’s my kinda town and it will be yours too in no time. This world-class city sits on the shores of tremendous Lake Michigan (so big, it looks like an ocean) where visitors are delighted by its lakefront beaches and parks, incredible restaurant scene, and world class museums.
What to Do
A first time visitor must head to Chicago’s newest outdoor space, Millennium Park, right downtown where you can see free concerts at the Frank Gehry-designed band shell, dine al fresco in the lovely beer garden (or ice skate right here in winter time!), and of course check out the wondrous and selfie-worthy reflective sculpture known as the “Bean”.
Rent a bike at one of the hundreds of stations all over the city and head to the lakefront path for a ride past volleyball courts, harbors, a golf course, and even a wildlife sanctuary. Hit the water by taking a boat tour on either the lake or the Chicago River where you will marvel at Chicago’s incredible architecture and massive skyline.
For a bird’s eye view of the city, head up inside one of North America’s tallest buildings, the Willis Tower (formerly Sears Tower) to the new Skydeck Chicago for some hair-raising views.
A stroll on beautiful Michigan Avenue is a must-do for shopaholics.
Every neighborhood has its own local and unique flavor–If you have time, check out some of my favorites like hipster hangout Wicker Park, baseball-themed Wrigleyville, Swedish-centric Andersonville, and heavily German influenced Lincoln Square.
Where to Eat
Over the last decade Chicago has grown into one of the world’s best cities for dining. This city literally has it all – from Thai and Greek to Ethiopian and Vietnamese, nearly every ethnicity is represented here. Plus there’s something for every budget from the famous Chicago Deep Dish pizza, hot dog stands, and corner noodle shops to Michelin Star and James Beard Award winning chefs and bistros.
Something for every budget
If you’re staying downtown, a stop in at Rick Bayless’ XOCO is a must for some affordable gourmet Mexican cuisine. There will likely be a line at this popular, counter-service spot, but it’s well worth it when you sink your teeth into the guacamole, amazing tortas, and decadent Mexican hot chocolate.
For that once in a lifetime’ treat, make reservations at Girl and the Goat, overseen by Top Chef winner, Stephanie Izard. The vibe is warm yet industrial and the food is some of the best around, really showcasing what the Chicago food scene has to offer.
Where to Sleep
Chicago has tons of hotels to choose from and more and more go up each season. Whether you’re looking for a simple budget option, a business hotel with all the amenities, or more of a cool, destination hotel with great bars and restaurants, Chicago has something for everyone.
Looking for the best places to find shelter from the wind of Chicago? Check out our trivago picks for best Chicago hotels!
Some of the newer, luxury hotels include the brand new Langham, built into the landmark IBM building with a mid-century vibe right on the river or the Trump International Hotel and Tower. Find out more about staying at the Trump here!
There’s been a wave of new, boutique hotels as well. The James and theWit are a bit more trendy, but even if your budget doesn’t allow a stay there, head up to the rooftop bar at theWit for a crafted cocktail and some amazing views right in the heart of the Loop. If you’ve got your heart set on staying at theWit, see more info here.
Photo by Tony Webster
- Rent a Divvy bike. There are now thousands of bikes for rent located all over the city. Chicago has an extensive network of bike lanes on most streets and the fact that the city is completely flat makes it even easier to get around.
- Take the CTA trains and buses everywhere. No need to spend money on taxis with a good network of trains.
- If you need a taxi, try UberX. Just download the app to your phone.
- Get out of the city center. Chicago is a city of neighborhoods, each one with its own unique vibe and charm. Take some time to head out and see where locals like to live and play.