Only in Chicago
How to spend three days in the Windy City
In the way people like little treats, I love little getaways.
Fall is my favorite time to explore with cooler weather and changing leaves abound. As I head out on these adventures the next few weeks, I’m going to share them with subscribers, including my itineraries. Starting with one of my favorite destinations: Chicago.
If given the choice between New York and Chicago, at least half of the time I’ll pick the latter. Chicago has everything I’m looking for in a big city. A great food scene, easy access to the waterfront (both river and lake), and good public transit. Plus, people are so much nicer than they are in New York. I’m almost never ready to come home. Now I just need to convince someone in the book publishing industry to open an office there…
Here is your breakdown to making the most of a three-day weekend in Chi-town.
Friday Morning
The flight from New York to Chicago is about two hours, long enough for a snack but not for a movie. Try for an early trip from LaGuardia so you’ll have the whole day to explore and fewer chances of dealing with delays. Once you land, it’s about $75 for a cab/ride share downtown, or you can take a blue line Rapid Transit Train operated by CTA for $5 or less. Either way is about 45 minutes.
Friday Afternoon
Located on Lake Michigan in the Streeterville neighborhood, Navy Pier is among the most visited attractions in the Midwest. The pier served as a naval training center during WWII but these days it’s a hub for recreation and entertainment, including a ferris wheel, carousel, and Shakespeare theatre. Stop by for a bite to eat (Harry Caray’s Tavern has simple, delicious sandwiches) then go for a boat ride with Shoreline Sightseeing. You have the option of a 45-minute cruise along Lake Michigan, or a 75-minute architecture tour down the Chicago River. Pick up some Garrett Popcorn before heading home.
Friday Evening
Chicago is known for its wealth of culinary creations, so no visit is complete without indulging in the scene. Tanta in River North serves up traditional Peruvian cuisine alongside strong drinks in a brightly colored, high energy atmosphere. Share a few antichucho (grilled skewers) to start, then try a wok dish for your main. Don’t miss out on trying a Pisco Sour, the national cocktail of Peru.
Saturday Morning
The Andersonville neighborhood is known for its one-of-a-kind shops, distinct eateries, and historic architecture. It’s also the hub for Chicago’s Swedish population. Head on over, grab a coffee from a café, and explore. Women and Children First is a fabulous feminist bookshop with a wide selection of reads for adults and kids. Milk Handmade features unique clothes and jewelry alongside high-quality candles. And Transit Tees produces locally designed souvenirs perfect to bring back as gifts.
Saturday Afternoon
A visit to Wrigley Field is a must during baseball season to cheer on the Chicago Cubs. It’s the oldest ballpark in the National League, and game days give you a great sense of the passion. In addition to seats within the stadium, nearby residential rooftops sell seats for viewing. If sports really aren’t your thing, you can just tour “The Friendly Confines” for $30 before grabbing a snack at a bar or restaurant in Wrigleyville. Perhaps a famous Italian beef sandwich or Vienna beef hot dog?
Saturday Evening
I’m not sure Chicago-style pizza really counts as pizza (sorry, not sorry). It’s nonetheless a quintessential part of experiencing the city. Two of the classic places to grab yourself some deep dish are Giordano’s and Lou Malnati’s. They have multiple locations, and lighter options like salads and thin-crust for the slightly faint of heart. Don’t worry: if you can’t finish, there are boxes.
Sunday Morning
You can take me out of New York, but you can’t take away my appreciation for brunch. A fun option for the weekend staple is Beatnik on the River. The Mediterranean restaurant offers global cuisine alongside fruity cocktails in a brightly-colored atmosphere right along the Chicago River. You’ll want to make a reservation in advance to assure a seat with a good view. Be sure to try the Piña Colada, too, served inside a coconut.
Sunday Afternoon
Have a lazy stroll down the Riverwalk to work off your delicious meal (trust me, you will be very full). Then turn and head over to Millennium Park for a look around at the grounds, including The Art Institute of Chicago. Yes, this is where you can see The Bean, or more formally Cloud Gate. Keep heading down S Michigan Avenue and you’ll find the Fine Arts Building, which on its second floor houses Exile in Bookville. Stop in and say hello to bookshop owners Javier and Kristin, as well as their valiant vinyl collection.
Sunday Evening
Loop back around to the Riverwalk and watch the sunset from a bridge, then stop in for a hearty meal at River Roast. Make sure to start with the shrimp and crab toast for the table. In terms of mains, the roast beef is phenomenal and sliced right in front of you. Same with the roast chicken. And save a little room for a sharable piece of chocolate layer cake.
Bonus Fun
If you’re visiting over a weekend during football season, a trip to Soldier Field—the oldest stadium in the NFL—is worth the hassle. Bears fans might not always have the best team to cheer on, but they definitely have good spirit. With a seat in the nosebleeds, you’ll get a view of the game as well as boats out on Lake Michigan.
Green City Market in Lincoln Park is a great way to spend a Saturday or Wednesday morning. Local food vendors set up tents of sustainable snacking options, everything from jam to cheese to bagels and more. Arrive early with an empty stomach to make sure you’re able to try everything.
Rachel’s Weekly Recs:
If you haven’t gathered from this newsletter, I travel a lot. This requires a superior carry-on bag. About a year and a half ago my partner gifted me the Monos Carry-On Pro Plus. It’s very pricey but can fit everything I need for a long weekend and more, no problem. Including formal wear. Plus the outside laptop pocket is truly *chef’s kiss*.
Life is Good has the most adorable fall t-shirts for the whole family. Some of them even glow in the dark! I’m especially fond of those featuring Winnie the Pooh. Treat yourself to a soft, cute treat as the seasons start to turn.
Stress has pretty much been my middle name lately, which means breakouts are constant. I adore this Clinique Acne Solutions Clinical Clearing Gel to dry up patches and heal spots in a matter of hours.