Do you like a big cosmopolitan city with small-town friendliness? Do you often wish that your slice of pizza was a little more substantial, as in not the flimsy New York pizza, but the hearty deep-dish variety?
Then you need to come to Chicago. It’s one of the best destinations in the U.S.
With its awe-inspiring architecture, beautiful scenery, and great food scene, the Windy City has as much to offer as any major town. And who can forget Lake Michigan? Even better, there are so many attractions here that are FREE. Millennium Park springs to mind - a veritable outdoor museum and gallery. Dozens of free museums are located throughout the city. If you happen to be here in July, do not miss the world’s largest food festival, Taste of Chicago. There is also a vibrant jazz scene here.
The Major Attractions
The major attractions include Willis Tower and Navy Pier. You can stroll the Riverwalk or take any number of cruises. Get a bird’s eye view from Sky Deck in Willis Tower (which was the tallest building in the world for 25 years.) Visit the Chicago Cultural Center, or take in a baseball game at Wrigley Field. The Field Museum of Natural History and the Lincoln Park Zoo is a great place for the entire family but the best thing to do is just walk the streets of the city.
Did you know that Chicago’s Second City comedy club produced some of THE most famous Saturday Night Live comedians! Make sure to catch a show when you’re in town. Who knows, you may see someone you recognize. There are multiple shows going on at the same time. If you know you’re coming to town, make reservations early and book the main stage. Tip: sit ‘on the rail’ and arrive early! And if you’re an aspiring comedian or writer, you can learn from the Second City pros in person or online. Second City
New York isn’t the only place to catch great on/off-broadway shows. Chicago’s historic and beautiful theaters like the Chicago Theater (great photo opp!) run the hottest shows and concerts year-round. Broadway in Chicago
Don’t forget Chicago at Christmas. It rivals New York in its decorations and vibe. The holidays in Chicago are magical!! The city transforms to a Christmas Wonderland - things you must see and do:
- Visit the Michigan Ave Macy’s and tour the whimsical window decorations and dine at the famous Walnut Room. The Macy’s building was formerly Marshall Fields and is chocked full of history!
- Chriskindlmarket - this Chicago holiday staple makes you feel like you’re in Germany! Enjoy sipping gluhwein, or mulled wine, eating a traditional mouth-watering pretzel, and strolling the endless maze of shops. Make sure to buy the annual mug as a souvenir!
- The Lincoln Park Zoo has the most spectacular holiday light displays in the city! Wait for it....and they’re free!
Pro Tip: If you go to Chicago in the winter bring plenty of clothes including face coverings and gloves. The wind coming off the lake can be brutal.
While Chicago’s nickname is “The Windy City” the name was not originally because of the wind coming off the lake. The most popular theory holds that it was coined in reference to Chicago’s bloviating residents and politicians, who were deemed to be “full of hot air” while competing with New York for the 1893 World’s Fair which Chicago won.
Where to Shop in Chicago
For shopping, the obvious choice is the Magnificent Mile. Here you will find everything from the flagship stores of Zara, Disney, and Nike, to interesting boutiques and high-end shops - all spanning eight city blocks. It is centrally located at or near most of the city’s attractions.
Other shopping can be had at the Pedway, a vast network of pedestrian tunnels, with many shops and restaurants. Don’t forget to grab lunch at Lou Malnati’s it’s one of the best pizza restaurants in the city or Pequod’s which is a local favorite. Pequod’s have pizza pans that are over 50 years old and you probably won’t see tourists in the place. This one is a gem you shouldn’t miss.
For those who love great deals, the Fashion Outlets of Chicago mall is very close to O’Hare International Airport. Make that your last stop to fill your suitcase or buy and pack a new one!
Off the Beaten Path Chicago
If you would rather not follow the throngs of tourists, there are plenty of great places to go where the average visitor would not think of going. Here are just a few:
If you’re are any kind of Wizard of Oz fan, you must visit this whimsical, Oz-themed park located in the Lincoln Park neighborhood. Stroll past Oz-themed amenities such as the playground deemed Dorothy’s Playlot, the statues that are scattered about the area. The Tin Man, Cowardly Lion, Scare Crow, Toto, and Dorothy herself stand proud here.
For those who enjoy a secret nightcap, mosey over to The Violet Hour, a speakeasy celebrating Chicago’s drink culture. If the bar is open, have a seat and reward yourself with a tasty beverage from the bar’s talented mixologists. Or order a home bar kit and make it a night in your room or Airbnb.
The Money Museum is located in Chicago’s Federal Reserve Bank. This museum attempts to make money fun with zany exhibits like a cube that contains a million one-dollar bills, and other eclectic displays, and we think it does a pretty good job. The reserve itself is a working currency center and fun fact: the bank regularly shreds around $10 million per day of old, unusable bills.
For the science aficionados, or for just the plain curious, be sure to visit the DNA Discover Center. Located in the revered Field Museum, visitors are invited to learn about all things DNA. It is a permanent exhibition within the museum that acts are a real-life DNA research lab, where scientists work every day to explore the building blocks of life.
Explore Chicago neighborhoods! Each has a flavor and vibe of its own and most have their own street festivals in the summer. A few you don’t want to miss include Well Street Art Festival in Old Town, Taste of Greektown, Taste of Randolph, Roscoe Burger Fest, and Retro on Roscoe.
If you want to be wowed, attend the Chicago Air & Water Show! Pack a cooler, stay the day, and prepare to be inspired!
TAKE THE ARCHITECTURAL tour down the Chicago River (but read Devil in the White City first : ) This is a must-do if visiting Chicago and it will finally answer the question, “Did Mrs. O’Leary’s cow really start the famous Chicago fire?’
Rent a ‘Divvy’ bikes and cruise along the lakeshore.
Millennium Park’s Hidden Garden – experience understated natural beauty in this urban Park. You won’t even know you are still in the city.
Chi-town has something to offer for everyone. You will no doubt stumble upon something not mentioned here that wows you and will leave you wanting to plan on coming back to this great city.
Where to Stay in Chicago
Let’s face it. Hotel costs in any major city can be expensive! But there are great deals to be had. If you are renting a car during your trip, try to stay away from the city center, where rates are highest. Look for hotels that are further out.
Acme Hotel Company. Voted #1 hotel in 2019 by Condè Naste, it is located just two blocks from Magnificent Mile. An ultra-hip hotel with minimalist décor and super-comfortable rooms with all the amenities and Serta Suite plush beds. And the best part? It’s super affordable. I have always found the service to be impeccable.
Club Quarters Hotel Chicago. For the budget-minded, this is the place to lay your head at night. The rooms are on the smaller side, but they don’t skimp on comfort. Located in the Central Loop in downtown, and offer studio suites with kitchenettes. There is an on-site restaurant and bar with an English Pub feel.
Ambassador Chicago. For an upscale option, the Ambassador is an ultra-stylish property with minimalist, modern rooms and an old-school glamour lobby with chandeliers. Some rooms offer fantastic city views and located on Chicago’s Gold Coast. Since 1926 it has hosted the likes of Frank Sinatra and Ella Fitzgerald
The Best Local Pubs and Eating Spots in Chicago
Chicago has some of THE best rooftop bars! While many may claim to have great views, here are a few that you and your camera will love:
When the jazz clubs reopen be sure to make the rounds. One of my favorites, Kingston Mines, and has been opened since 1968. If you love Jazz and Blues, you’ll love Kingston Mines.
Chicago Dogs and Italian Beef Sandwich’s – equal to Chicago pizza, these are ‘must-try’ meals for traveling foodies! You can get them just about everywhere BUT, visit Portillo’s and you will NOT be disappointed.
Bridgeport Coffee Company – for that morning lift, come get the best cup o’ joe in Chicago-land.
Aberdeen Tap – for yummy pub and grub, come to this fantastic local hangout.
Lou Malnati’s – this is Chicago deep-dish pizza at its finest. You will need to be carried home after a meal here.
Hoosier Mama Pie Company – if you DO still have room after that pizza, this insanely-delicious bakery serves the BEST home-made pies.
Pequods – this is a local deep dish pizza favorite.
Coco Club – a prohibition-style speakeasy with strong drinks and live music!
Casey Barbles 
Jeff Yelton 