For nearly two decades, Chicago has been one of my favorite places.
(And I’m only 26, so that’s saying something.)
To be fair, my first trip to Chicago at the tender age of 9 included my very first plane ride, a visit to the American Girl Place, and a restaurant where we roasted s’mores at the table. That’s a surefire way to make a kid fall in love.
Then my whole family visited. Then my boyfriend moved there. Then I moved there.
Last year, I lived in Chicago. I worked in one of the less touristy neighborhoods. I grocery shopped in the South Loop. I fought traffic on I90/94. And yet Chicago continued to earn its place among my favorite cities.
It has lovely lake views and it has world-class museums. It has a sweeping downtown skyline and the city center remains relatively walkable. It is Midwest-level friendly and it has big-city amenities.
Adam, remind me why we moved again?
If you’re headed to Chicago, you’re in for a treat. I want you to love the city as much as I do, so read on for my ultimate list of Chicago recommendations.
Downtown:
For the Views
An architectural boat tour. Chicago’s skyline is just the best. Sure, everyone is attached to their own city’s skyline. But Chicago is novel not just because it has a high concentration of cool buildings; it also has both a river and a lake for ultimate viewing potential. If you want to gaze at the skyline for free, walk to the end of Navy Pier. If you have more time and money, an architectural boat tour is absolutely worth it. The commentary is interesting, and the views are unparalleled.
If you have time, grab a Northman’s cider when you’re done. Drink it while you stroll along the Riverwalk and people watch.
360 Chicago at the Hancock Building Observation Deck. Any great Chicago itinerary needs to include an aerial view. The two top contenders for this are the Willis Tower and the Hancock Building. I gotta say, the Hancock Building wins for me. The Hancock is on the northern edge of downtown, so you’ll get you a better view of the entire skyline.
The Hancock also has the Tilt window, an attraction where you stand in a large window, death-grip the handrails, and try not to shriek as the window tilts toward the sidewalk. The angle does not look terrifying in photos. It is in real life.
It is a much better adrenaline rush than the clear floors at the Willis observatory. The lines at the Hancock are also shorter – if you don’t have fast passes at the Willis, you might lose your mind.
For the Culture
The Art Institute of Chicago. Ah, this place. Chicago has a great museum for any pretty much any interest. Local history? The Chicago History Museum. Beluga whales? The Shedd Aquarium. Dinosaurs? The Field Museum. But the Art Institute is the one I’m drawn back to most often. Every special exhibit I’ve seen there has been worthwhile. I could also linger for hours in its collection of Impressionist works. If you go, say hi to Paris Street; A Rainy Day for me.
The American Writer’s Museum. Among all the famous Chicago museums, this is a little-known gem. It takes up just one floor of a downtown building, but it gives a really excellent walk through the timeline of American literature. Old typewriters and fun interactive displays are a perk.
For the Architecture
Any thorough Chicago itinerary should include a visit to some beautiful buildings – the city has a large concentration of them. Here are some worth seeing.
Chicago Cultural Center. The Tiffany stained glass in this former library is stunning. The guided tour is only available a few times per week, but it is definitely worthwhile.
The State Street Macy’s. Admittedly, I have an attachment to this one because I bought my wedding dress in its bridal salon. But it’s also worth seeing for the building itself. This was once the site of the Marshall Field’s flagship store. Though it’s now a Macy’s, the iconic clock and gorgeous mosaic ceilings remain.
The theaters, concert halls, and opera houses. These venues are worth it for the shows, absolutely. (If you haven’t seen Hamilton, stop everything and start saving your pennies.) But the architecture is an excellent bonus. Lyric Opera House is top of my list.
The Palmer House. The original hotel burned down in the Chicago Fire only 13 days after it opened. The developer completed a new building designed to be fireproof, and it’s still around. I recommend spending time in the decadent lobby (and ordering the fries and the flatbread from the bar).
The Rookery. Frank Lloyd Wright designed the airy lobby of The Rookery, making it more than your average office building. This would be great paired with a tour of any other Frank Lloyd Wright houses.
For the Food
Cindy’s. This is the rooftop bar on top of the Chicago Athletic Association Hotel. It’s an amazing venue with views of Lake Michigan and the Bean, plus splurge-worthy food. Brunch is slightly more cost-effective than dinner. Either way, make reservations way, way ahead of time.
Stan’s Donuts. This donut shop has multiple locations throughout downtown. Get the donut with the Biscoff pocket, ohmyword.
Pequod’s. People get feisty about their Chicago deep-dish opinions. Here’s mine: if I need a chain with multiple locations, I go to Lou Malnati’s. If I can go out of my way, have time to wait in line, and want the best caramelized cheesy crust in the world, I go to Pequod’s.
The Goddess and the Baker. Two different downtown locations serve good food and even better Hot Mama Elixir (hot chocolate spiked with cayenne). I lick my cup clean every time.
Eataly. This Italian marketplace has something for everyone. There’s a counter for quick bites and a gelato stand on the first floor. Head up to the second floor for a seasonally themed bar, a pizza and pasta restaurant, and a more upscale spot for 3-course meals. Even their most basic pasta was delectable. If you have room in your carry-on, you can also shop the imported olive oils, pastas, and other Italian deliciousness.
In Hyde Park:
Chicago has countless neighborhoods that are well worth a wander. Lincoln Park has the houses of my dreams. Pilsen has tons of up-and-coming restaurants. The Wicker Park/Bucktown area has an artsy vibe.
Of all those neighborhoods, I urge you to catch a Lyft down to Hyde Park.
Yes, I am biased. My husband and I lived in Hyde Park when he attended graduate school, and we loved it. If you know anyone who goes to the University of Chicago, or you think you might want to attend there, or you like great architecture, or you find science interesting, or you’ve read about the Chicago World’s Fair, or you enjoy Lake Michigan, we think you might love Hyde Park, too.
Here are our neighborhood favorites.
For the Views
The Carillon Tour at the Rockefeller Chapel. The University of Chicago is home to the first nuclear reactor, a surprising number of Mesopotamian artifacts, and the second largest musical instrument in the world. That instrument is the carillon. What’s a carillon? It’s the 72 bells hanging above the Rockefeller Chapel. On the carillon tour, you’ll climb half a bajillion stairs into tower. You’ll get to see the bells and watch students play the Jurassic Park theme song. You’ll also get excellent views of UChicago’s gothic buildings, Lake Michigan, and the downtown skyline. Tours are only held a few times a week, so check the schedule.
Promontory Point. This park is one of the dearest spots in all of Chicago. The point sticks out into Lake Michigan, offering splendid views of downtown a few miles up the shore. On windy days, watch waves smack against the point and try not to get splashed. On calm days, dip your toes in the water (or head down the sidewalk to the beach for an actual swim). The Chicago Lakefront Trail also runs past Promontory Point. Bike rides from downtown would be feasible for riders with a bit of stamina.
For the Culture
The Museum of Science and Industry. MSI is the only building remaining from the Chicago World’s Fair in 1893. Originally built as the Palace of Fine Arts, it was fireproof and sturdier than the other temporary plaster buildings. It now contains some really excellent science exhibits. The U-505 exhibit remains one of the most impressive exhibits I’ve seen in any museum. Colleen Moore’s Fairy Castle is also an underrated spectacle. After wandering through the museum, World’s Fair enthusiasts should walk just south of the museum. There, you’ll find the Osaka Garden, a replica of the Fair’s Japanese garden.
The bookstores. Like any good university neighborhood, Hyde Park has some really great bookstores. I love 57th St. Books the most for its garden-level quaintness and excellent selection. If you want more, wander down the street to Powell’s Used Books, an institution that plays a significant role in the middle-grade novel Chasing Vermeer. Then head toward campus for the Seminary Co-op, which has a great nonfiction selection and hosts lots of readings and discussions. If you’re in Hyde Park in the fall, also watch out for the spectacular used book sale.
For the Food
Fabiana’s. In the good ol’ days, I lived within walking distance of the best cinnamon rolls ever. (Nab the day-old ones for a discount.) Make sure to get it warmed up!
The Promontory. I dream of the Promontory brunch menu, though they have a great bar and dinner menu, too. Go for the hip atmosphere, stay for the breakfast potatoes.
The Bibliophile. This book-themed restaurant was possibly designed for my husband and me. The walls are lined with books that you can read and purchase, and the menu offerings are excellent. We’ve only tried their desserts and drinks, though they now have brunch, dinner, and afternoon tea available as well. If you like chai and orange, the Alice in Wonderland is one of the most unique cocktails I’ve tried – like a grown-up Russian Tea.
Other Travel Tips
City Passes. The Chicago CityPass or other pass deals can be great if you’re hoping to hit most of the major attractions on a busy weekend. I’ve only done the CityPass, but this article has a good guide to the options.
Parking. Parking in Chicago is a beast. If you can get by without a car, do it. Ubers and Lyfts (typically the cheaper option) abound, and the El can get you most places around downtown. If you have to drive, download the SpotHero app to help find discounted parking. Do not ever pay the standard garage rates if you can help it.
Lodging. The perks of staying downtown? Easy walking access to most attractions, and potentially great views of the river or lake. The perks of staying anywhere but downtown? Cheaper rates, avoiding hefty valet fees, and being able to take public transit into the city. Pick your poison!
Needing more Chicago recommendations? This list is by no means exhaustive. On our next return visit, we’d love to check out the Garfield Conservatory, Au Cheval for their life-changing burgers, the Green Mill for live jazz and gangster references, and Mindy’s Hot Chocolate. I also like following local bloggers like @chicagoismyboyfriend for under the radar ideas.