Chicago is the third biggest city in the United States, and full of sights to behold. Between the cultural contributions, beautiful architecture, easy to navigate public transportation and old city feel combined with modern amenities, it’s one of my favorite places I’ve ever visited. We flew out for a quick weekend getaway, and left planning our next trip to do everything we missed!
Tips for visiting Chicago in November:
- Dress warm. Do not crowd your carry on with multiple outfits, but instead with hats gloves and coats. It’s cold, but not uncomfortable if you’re dresses appropriately.
- Don’t rent a car. The train will take you everywhere.
- Don’t stay in the city. Chicago had such cool neighborhoods, so do some research and stay in one outside of downtown for the full experience.
- Do all of the touristy stuff, then plan another visit for the underground, way cooler stuff.
Here are my top ten favorite things from The Windy City:
1. Wicker Park
We stayed at a cute studio apartment steps from the train station and a half hour train ride from O’Hare airport. Wicker Park is a hip little neighborhood with tons of vintage shopping, amazing restaurants and fun nightlife. It’s only a few L stops away from Downtown, so getting around is a breeze. My favorite spots were Dove’s Lunchonette where you can get breakfast and a tequila flight, and Stan’s Donuts, a more low key and delicious version of Voodoo.
2. Chicago’s First Lady Architectural Boat Tour
Chicago is like a playground for architects, and a boat tour is a must for seeing the buildings up close. Even though it was chilly, if you dress appropriately the 1.5 hour boat tour is a great experience (they have a heated saloon and bar underneath!). We learned all about the how the Great Chicago Fire destroyed the city in the 1800s and literally paved the way for a new impressive skyline. They continue to blame the poor Irish immigrant Mrs. O’Leary and her cow for the fire, but I’m now under the impression it was a giant government conspiracy to build Chicago into a amusement park for architects. I highly recommend The Chicago First Lady tour; it is run by the Architecture Foundation and the tour guides are super knowledgeable about the history of the buildings.
3. The Untouchables Gangster Tour
When you think of Chicago, you think of Al Capone and his merry band of criminals. This tour is led by a bunch of guys with criminal alter egos (we got Johnny Three Knives and Shoulders) who give you a colorful history of Chicago’s gangster eras while taking you through neighborhoods where famous killings happened. They’re extremely animated and never break character, even with only 4 guests on the tour (us and a couple from Alaska who were not impressed we had just been to Alaska at all). It’s a mix of kitsch and history, and you might win a prize during their raffle, or be included in a traditional Italian sing a long.
4. Willis Tower
Definitely something you should do once, just not at noon on a Saturday, unless you love standing in hour long lines. The Fast Pass is about $50, and is definitely worth skipping the line if it’s hours long…did I mention I hate standing in HOURS LONG LINES?!? The former Sears’ headquarters was at one time the tallest building in the United States, recently beat out by One World Trade Center. The views from the top are breathtaking; you can see the entire city and sometimes the three surrounding states if it’s clear. Be prepared to stand in another line to get out to the Sky Ledge, and then at least 10 minutes to muster up the courage to step out while the other line waiters get annoyed.
5. Eat Chicago Food
Whenever I go somewhere new, I feel obligated to eat the “local food” even though I’m aware it’s the most touristy thing to do (like Philadelphia…get the cheesesteak — PATS NOT GINOS– then find all the other good food they have to offer). But Chicago dogs and deep dish pizza are actually delicious. We went to Devil Dawgs in Wicker Park to chow down on a pickle/tomato/Poppy seed bun, and Gino’s East Brew Pub for a pizza served in a skillet with mounds of tomato sauce on top, and were not disappointed (but maybe a little heartburny).
6. Take the L Anywhere & Everywhere
Growing up in Delaware, I never realized that people actually use and get where they need to be via public transportation. In my opinion, Chicago’s elevated train system is the easiest to use of any large cities. For $20 you can get an unlimited 3 day pass, and trust me you will get your use out of it. We took the train from the airport to our air BnB, from the air BnB to downtown, from downtown to uptown, and then back to the airport with no troubles at all. Compared to LA where we waited for a train for hours (that never came), and New York where you have to be a cartographer to navigate the different lines, Chicago wins my vote for most accessible public transit.
7. Wrigley Field
Even though baseball is not my sport, it’s cool to see the 2nd oldest ball park in the nation up close. It’s set right in a neighborhood with tons of little sports bars, and is right off the Addison stop on the red line.
8. Green Mill Lounge & Uptown
A few stops away from Wrigley is an artsy section of Uptown with a jazz club , The Green Mill Lounge, formerly owned by Al Capone. It has no dress code, a great 20s speakeasy vibe and nightly jazz that pays homage to the ghostly musicians who played there in their heyday. Green Mill doesn’t serve food, but there are several restaurants nearby, including my personal fav Fat Cat with yummy elevated diner food.
9. Navy Pier
In the summer, Navy Pier is packed with tourists but on a chilly November day we had the place to ourselves. There are restaurants and shops, plus a breathtaking view of ocean-like Lake Michigan. The Centennial Wheel, modeled after the first Ferris Wheel created for the World’s Fair, it features enclosed cars and a gorgeous view of Chicago’s skyline so you can enjoy your ride in heat or air conditioning year round!
10. Millennium Park
You must see the bean, aka Cloud Gate, an art sculpture added to Chicago in 2004. It’s weird and beautiful and trippy underneath. Millennium Park has great walking paths and other art installations to look at, like the Jay Pritzker Pavillion, and Crown Fountain, plus Chicago’s beautiful Christmas tree in the winter.
Things I Didn’t Get To Do and Will Be Returning For:
Tiffany Dome: Ok I thought this was in Macy’s, and found a ceiling I assumed was it, especially because some guy recommended I go to the 5th floor to get a closer look. So the ceiling (pictured below and incorrectly captioned) in the Michigan Avenue Macy’s is worth seeing. But the real Tiffany’s dome is nearby in the cultural center, and if you hear about a heist job, it was me.
See a sports game: Chicago is home to some of the most loyal sports fans in the world, so catching the Cubs at Wrigley or the Bears at Soldier Field is probably a sight to behold in itself.
See a show: Chicago has a huge theater district, and had more time allowed I would have been front row at Escape to Margaritaville, what I can only assume is a tribute to Jimmy Buffett.
Shop on the Magnificent Mile: I’m ashamed to say I bought nothing on this trip, except my usual magnet and souvenirs for Aimee and Steve. An extra day would have been perfect to add to my big city Tiffany’s collection, so I’ll be back.