I have only been to Chicago twice, and both times were for just a few days in the month of October. But that’s all it took for me to fall completely in love with it. I titled this Eat+Stay+Play guide “Chicago, City of Appetites and Architecture” because it was those two things that made the biggest impression on me this time. I even wrote an entire blog post on the architecture alone and included some amazing photos of buildings you just don’t see every day (you can read it here). And if you want to see all my E+S+P travel guides, go here.
Needless to say, the Eat and Play sections will dominate this guide. We spent 3 full days and 2 half days in the Windy City and didn’t leave the downtown area. There was that just right amount of chill in the air that I think makes a big city come alive.
Chicago was once known as America’s Slaughterhouse, and it probably still has a little of that vibe (I’ll never forget reading The Jungle for the first time – woa). That being said, it’s a great place for incredible food and top-tier steakhouses on seemingly every corner. Although I’m more fond of New York style pizza, Chicago-style hotdogs are where it’s at. My favorite place to indulge in these loaded dogs is Portillo’s but the Chardog at Gold Coast Dogs is really good too.
If you’re just looking for a great snack, I highly recommend Garrett Popcorn Shops. You have to get the Garrett Mix, also referred to as the Chicago Mix. It’s an equal mix of caramel popcorn and cheese popcorn and it’s absolutely wonderful. I’m actually salivating just thinking about it. If you can’t get to Chicago, you can always order it online. It would make a great gift this time of year, too.
My favorite dinner spots include:
This is the epitome of the modern steakhouse. The interior design is just the foreplay to the decadence to come. Dark walls are accented with larger-than-life photos of raw cuts of beef and octopus, lit just enough to spark curiosity about the adventurous menu. I recommend starting with the beef tartare and the brussel sprouts with jamón ibérico. Follow that with the Carnivore, a carved platter of beef filet, beef strip loin, venison, and American Wagyu. Leave your vegetarian friends at home.
If you’re after a little more of an old school steakhouse feel, then Chicago Cut is it. There’s an impressive selection of seafood in addition to steaks. There’s even a dry aging room. Start with cocktails in the bar (the martinis are perfectly strong) and then enjoy riverside views from your plush red seat in the dining room.
For casual dining and a bit of history, try The Berghoff. This is the home of Chicago’s first ever liquor license. If you don’t feel like a full German meal, at least get the giant Bavarian pretzel. It arrives hot and hanging from a hook above a trio of dipping sauces and mustards. You can get one to share or do the smart thing and just get your own. It’s incredible!
This is also a great spot for dinner, but we enjoyed a casual lunch sitting at the bar. It’s the kind of lively bar atmosphere that is both festive and cozy. It was almost like being in a movie, if that makes sense. I had the best Chicken Milanese here with sparkling rosé. Cocktails and service are excellent.
Located right by Millennium Park is The Gage. I immediately loved the design aesthetic of dark wood, brick, subway tile, and bronze lighting. Then there’s the amazing food. You must try the Potted Stilton Cheese. It’s decadently smooth and served with warm crispy ciabatta. They also have a great selection of craft beers, including some local Chicago brews. Head over to “The Bean” when you’re done.
Breakfast and/or coffee break:
I found this charming coffee shop just outside the Harold Washington Library Center. It was the perfect refuge from the cold and the coffee is on point both in taste and Instagramability. I also enjoyed a hot breakfast sandwich that was just about as homemade as it gets. There’s plenty of seating and places to work if you need to bring your laptop.
We stayed at The Palmer House Hilton, an historic hotel that has been in continuous operation since it was rebuilt after the Great Chicago Fire of 1871. The interior is really impressive with a high ceiling fresco that could easily compete with frescoes across Europe. I felt like I should be wearing a flapper dress, sipping champagne from a shallow coupe and saying things like “Old Sport.” It’s quite beautiful and the rooms are comfortable. Don’t miss the Peacock Doors adorning the entry, and make sure to order their famous brownie – it’s where it was invented!
Other swanky locales to hang your hat:
Among limitless luxurious amenities, The Langham offers guests private access to The Langham Club. This lounge offers things like afternoon tea, premium bar service, and spectacular views of downtown Chicago. There’s even a Writer’s Corner with reading library. Also, if you collect hotel pens like I do, The Langham’s pens are pink and oh-so-chic.
I definitely have a thing for historic hotels. This beaux-art beauty was built in 1920 and retains all of it’s original glamorous feel. It is here that Marilyn Monroe and Joe Dimaggio carved their initials into the hotel’s wooden bar. Afternoon tea in the Palm Court is a must.
The first activity we did when we arrived was to catch an architectural tour aboard Chicago’s First Lady, a boat cruise offering tours by the Chicago Architecture Foundation docents. This is the best way to see downtown Chicago, bar none. We had a beautiful clear day and enjoyed sitting on the top deck as the docent recounted tales of Chicago’s past and elaborated on the history of the buildings that make up its unique skyline. Even if you’re not overly interested in architecture, just sit back and enjoy the slow ride up the Chicago River all the way to Lake Michigan and back. You’ll at least have some great photos, and did I mention there’s a full service bar on board? But I think by the end you’ll have a new appreciation for building design and the architects who made the impossible possible.
Other sights and activities I recommend:
Yes, this is the home of the famous “Bean” sculpture, or as it’s officially known, “Cloud Gate.” This is a fun spot for kids of all ages and probably holds the world record for number of selfies taken in a single second. There are other art exhibits in the park throughout the year as well.
Even if you don’t catch a show here, you at least have to visit to see a historic theater’s 1921 grandeur. I recommend seeing it during the daytime and at night when the marquee is lit up.
I always make it a point to visit the public library whenever I travel. I love seeing a commitment to free information for all (I used to be a librarian, you know ;-)). Before you step inside, be sure to check out the incredible owls looking down at you from the top. Read more about these owls in my architectural tour of Chicago post. This library has a really cool makerspace for people of all ages to come and use laser cutters, 3D printers, computer modeling software, and crafting supplies. There’s so much creativity happening in one room. I also thought it was neat that there are music practice rooms available.
If you’re bringing your kids, this is a fun and free place to learn more about our nation’s currency. There’s a million dollars in cash on display and you can take a free commemorative photo at the end.
Go on a Walking Tour
Whether you go on an officially guided tour or just grab your camera and venture out alone, walking the streets of Chicago is a great way to spend your time. Take a stroll down Michigan Avenue, pop into shops like the original Marshall Field (now Macy’s), and find your inner photographer.
The Chicago Blackhawks were in town during our stay and we managed to get tickets last minute. How often do you get to experience hockey in Texas?
I hope you enjoyed this travel guide for Chicago. What are some of your favorite things to do in the Windy City?
For your Pinning Pleasure:
Eat+Stay+Play: Chicago, City of Appetites and Architecture appeared first on Cathedrals and Cafes.