One of chef Stephanie Izard's (from Top Chef) famous Chicago restaurants. Make an online reservation early. This one can fill up months in advance. If you can't get a reservation, try the smaller, less fancy Little Goat Diner in Lakeview. (Close to the Southport brown line stop).
Phenomenal burgers! This place does not take reservations. If you go on a Friday night, put your name in and expect about a 2 hour wait If you can't get in here, there are at least three additional Small Cheval locations in Chicago.
More accessible and affordable spot for brunch or dinner. (As you can tell, all the great Chicago restaurants are in Fulton Market. You can't go wrong with any of them!)
For brunch! This is along the Chicago River walk. Probably about a 20 minute walk from either wedding hotel. Molly was tipped off about this place because a few of her Cristo Rey students worked here. They kept talking about their job at school. She took their recommendation, and they were right. The food is good!
The two foods Chicago is famous for: pizza and hot dogs. Chicago pizza places are also the easiest places to eat without a reservation and if you have a party of more than 6. For pizza, take your pick! You can find a number of Lou Malnatti's or Giordano's. Recommended smaller joints would be Pequod's or The Art of Pizza (which sells deep dish by the slice). Molly has never liked ketchup, which is perfect because Chicago dogs do NOT come with ketchup. The best part of the Chicago dog is the celery salt, in Molly's opinion. You can get a Chicago dog at many locations, but a favorite one is The Wiener's Circle in Lincoln Park. Their cashiers are famous for serving a Chicago dog with a side of sass.
If you are walking downtown Chicago, you gotta hit up the Primark. (This is a clothing store, not a restaurant). Ok, so this is really just a bigger, better H&M, but it was the FIRST Primark to open in the United States. If you have been to Primark in Europe you know that is a big deal. On your walk there, go by the Joffrey Ballet at the intersection of Randolph and State. LOOK UP and you might see the ballerinas on the second floor exercising at the barre. (Molly's favorite thing to look for).
Top of the Willis (formerly Sears) Tower, with observation decks overlooking the entire city. Roughly $30 per adult ticket.
An iconic Chicago attraction. Cloudgate (aka The Bean) has been closed off for renovations for months, but it is supposed to open spring 2024. I anticipate it will be even shinier than before! Walk along the big lawns. Take pictures with The Bean and the big fountain with the spitting face. Keep walking towards the lake to go through Maggie Daley Park. If you have lots of time, stay for a round of Chicago-themed mini golf.
Get yourself to the lake and walk, run, or bike any stretch of the 18.5 mile lakefront path. this is one of Chicagoans favorite things about the city. If it is a hot summer day, pull over at one of the beaches and dip your toes (or yourself) into Lake Michigan. City DIVVY bikes can be rented if you download the DIVVY app on your phone. Have small cash or Venmo ready for the ice cream man who will be pushing his cart along the beaches.
Take the brown line or red line north and get off close to Wrigley Field. Take some pictures in front of the marquee! Even though the Cubs are not in town during our wedding weekend, Wrigleyville is always a happening place. Walk along Clark St and step into the bar that calls your name. Sluggers has indoor batting cages (in the bar!) and Lucky's has great sandwiches. If you feel overwhelmed, just go to the rooftop at Old Crow. Order the mac and cheese brisket sandwich.
Take the pink line to the Damen or 18th Street stop. Pilsen is famous for their street art. Go for a stroll and admire the beautiful murals. Obvious points of interest would be Cristo Rey Jesuit High School (where Molly works) and Harrison Park (where Molly coaches Cristo Rey teams). Consider stopping at the free National Museum of Mexican Art. For a bite to eat, 5 Rabanitos is more of a sit-down Mexican restaurant. (Owned by a Cristo Rey family that worked with Chef Rick Bayless). For quick street tacos consider Los Comales, Atotonilco, El Milagro, or Carniceria Maribel. (This one is on the corner of Cristo Rey's block. Walk through the small grocery store to the back. Great tortas, burritos, and tacos).
Molly's current neighborhood. Take the brown line north, get off at Paulina and walk west on Roscoe. This strip has great brunch places, wine bars, and book stores. Walk down Addison to get to Roscoe Village Pub (where Molly and Nick met!) This is just your classic Chicago corner bar: drinks at the bar, sports on TV, open patio out back.
If you have a hankering for authentic dumplings, hot pot, dim sum, bao or bubble tea look no further. Take the red line south to Chicago's Chinatown. For dim sum, go to Cai (it is a Cristo Rey tradition). If you have the time, walk all the way to Ping Tom park. Check out the different gardens and watch the trains go by on the elevated bridge.