If the Orioles were in town, we’d be having the wedding during the 7th inning stretch on the pitcher’s mound, but alas the Cubs are playing the Pittsburgh Pirates. If you feel like taking in a game at this historic ballpark, we recommend hopping on the CTA Red Line to Addison to avoid game day traffic (which can be brutal). It’s about a twenty minute train ride away from the hotel blocks. It's cutting it too close to the wedding to catch the Saturday game, but there are afternoon games on both Friday and Sunday. We recommend that you wait to see how the Cubs are doing before buying tickets. If their season's over by early September, you'll be able to snag cheaper tickets.
If you haven’t read Devil in the White City by Erik Larson, put it on your summer reading list and then get tickets to the Chicago Architecture Association’s riverboat architecture tour. It’s a 1.5 hour tour where you’ll learn about the history of Chicago as told through the city’s skyline. Chicagoans will tell you that this is the one touristy thing we can’t get enough of, and everyone’s done it at least twice because you always learn something new depending on which volunteer tour guide you get. We recommend getting tickets ahead of time on their website (linked) to avoid long lines at the ticket booth.
The iconic Cloudgate (aka “The Bean”) is the main attraction of Millennium Park, but be sure to explore all of the rotating art installations as well. Battle the crowds to get a picture of your reflection in The Bean, and don’t forget to walk right under it and look up to see your reflection cascade across the different facades. It’s cheesy, but it’s classic Chicago and something to definitely check off your tourism list.
One of our favorite views of Millennium Park and Lake Michigan is from the balcony at Cindy’s Rooftop on the top floor of the Chicago Athletic Association Hotel. A great way to spend an afternoon is to pair a walk through Millennium Park with a cocktail at Cindy’s afterward. Head downstairs to the Game Room at the Chicago Athletic Association to grab a quick game of bocce ball, chess or pool.
Jillian truly thinks the mile-long stretch of Michigan Avenue filled with retail is magnificent, but Jared may beg to differ. Regardless, if you’re looking for last minute cuff links or the perfect pair of earrings, this is where you’ll want to go. Work your way all the way to the top of the street and you’ll be rewarded with gorgeous views of Lake Michigan. You can even catch a tunnel to the Lakeshore path from the northernmost point of Michigan Avenue.
The Signature Room on the 95th floor of the John Hancock building is a great way to see the sweeping coastline of Chicago from indoors. Insider's tip for the ladies - the best views are from the floor to ceiling windows in the women's restroom. Sorry gents, but your bathroom faces inward. For the thrill seekers, check out the new TILT 360 ride while you're there.
Visiting Lincoln Park Zoo and neighboring Lincoln Park is a lovely way to spend a beautiful fall day in Chicago. Take a walk along the Lakeshore path and you'll see some of the most iconic views of the city just from outside the zoo.
There are two seasons in Chicago: Winter and Festival Season. Every weekend from May until mid-October the city is littered with different street and music festivals to give citygoers a chance to explore different Chicago neighborhoods. The weekend of our wedding is the Lakeview East Festival of the Arts. It's a bit of a schlep, but features 150 independent artists showcasing paintings, sculptures, photography, jewelry and more. Definitely worth a trip on the Red Line CTA if you're feeling inspired after the Art Institute!
Besides festivals and patios, the best thing about Chicago is hands down the food. Chicagoans love to eat, and the city delivers with world class grub. Here are some of our favorites: Best Burger - Au Cheval Get the burger. With egg. And bacon. Ask us how to strategize for this one, since the wait can be anywhere from 2-4+ hours. But trust us, it's worth it. Best Old-School Chicago Steakhouse - Joe's Stone Crab There are a few of these scattered across the country, and being in the Midwest, this one boasts a fantastic steak. Make reservations ahead of time if you want to indulge in this splurge-worthy evening. Best New-School Chicago Steakhouse - Steak 48 Most Chicagoans frown on new, trendy steakhouses, but man were we all surprised with how great a steak this places serves up. Quickly becoming a must-try spot, Steak 48 serves its steaks on sizzling hot plates that locks in the flavor with the perfect sear.
Best Deep Dish - Lou Malnati's While everyone has a different (and strong) opinion on the best Chicago deep dish, our favorite is Lou's. Their butter crust makes all the difference. If you're part of the keto club with Jared, they even have a crustless pizza (basically sausage, sauce and cheese...it's delicious). Best Chinese - Duck Duck Goat Stephanie Izard is a local, James Beard award-winning chef whose soup dumplings are out of this world. We love this spot for Sunday dim sum or a family style evening meal. Best BBQ - Green Street Smoked Meats Grab a tray and go down the line picking out all types of meats, from brisket to pastrami (dare I say it, almost as good as Katz's). If the line's long, grab a cocktail while you're waiting at the center bar. Best Sushi - Sushi San OR Sunda This one's a tie (because we love sushi so much, we can't pick just one). Check out either one of these River North hot spots for fantastic rolls, robata and cocktails.