We are so happy to welcome you to our wedding in the greatest neighborhood in the world, in the greatest city in the world.
In addition to well-trod hits like the Bean, Navy Pier, and the museums, Chicago is absolutely bursting with exciting and interesting things to see and do. Kevin will happily provide you with a bespoke itinerary to ensure you get the most out of your time here, but here are some particular favorites.
You don't need to get to the venue until 4:30, so we recommend getting to Lincoln Park early and enjoying the day there. Here are some ideas:
Take the Brown Line to the Armitage stop. Walk one block east down Armitage to Bissell Street, and get some delicious ice cream or Italian ice at Annette's. As you enjoy your treat, walk east down Armitage and through Oz Park, where you will see statues of Dorothy, the Tin Man, the Cowardly Lion, and the Scarecrow, and can go for a stroll through the Emerald City gardens. (There's a playground too, if you have kids or still feel like one.) If you're curious, you can wander before Oz Park down Burling Street to the south of Armitage, which hosts the city's most expensive homes, some of which are timeless marvels and some of which are monuments to the gauche.
From Oz Park, go east down Webster for about ten minutes and you'll run into the Lincoln Park Zoo, which has gorillas and is free. Nice. Be sure to take a walk around the nature boardwalk before you leave. If you share Lisa's love of green things, the Lincoln Park Conservatory (tree place) is right there as well, is also free, and has sausage trees and other prettier but less hilarious flowers. (N.B.: although the conservatory is free, you should reserve a spot online in advance if you are set on seeing it. They manage foot traffic, and often sell out on weekends. Labor Day Weekend will probably be busier than usual.)
After the zoo and conservatory, walk across the street to the Hotel Lincoln and take the elevator up to its rooftop bar, the J. Parker. Enjoy a cocktail and a view of downtown and Lake Michigan. (N.B.: this is a much less stressful affair than going to the more-famous Cindy's rooftop downtown. That place is always packed and loud and annoying.)
The wedding venue is just under a mile north of the J. Parker. You can walk up Clark Street (namesake of the Cubs' mascot) and enjoy the bustle of Chicago's main artery or walk through the park a block to the east.
Clark has lots of places for a bite or a drink if you want one. There is also a store that sells candy from all over the world and, more importantly, has the Teenage Mutant Ninja Turtles in Time arcade game, and it's free to play. So that should fill up about four hours of your day by itself.
If you have a few minutes to kill before getting to the venue, pop into Galway Arms, one of Kevin and Lisa's favorite haunts and the host of their engagement party, for a pint. Great craic in there. Then just turn the corner and you'll be at Salvatore's.
You can also just spend the day in the actual park after which the neighborhood is named. Lincoln Park is Chicago's biggest park (300 acres larger than Central Park) and is always teeming with dogs, kids, 19th-century baseball re-creationists, and general good vibes. Start at the fantastic Chicago History Museum (and go inside for a bit!) and walk north. You might enjoy seeing the turtles and the butterflies at the Nature Museum along the way.
(This itinerary starts in Lincoln Park, but the Path runs along the whole city, so you can also pick it up if you're staying in River North. Maybe stop at one of the bike rental places so you can snag some wheels and ride to the more interesting parts of the Path further north.)
The Lakefront Path is a real treasure, loved by bikers, walkers, and joggers alike. There are access points all along the path. If you're in the Lincoln Park area, walk east down Diversey until it ends. Start by stopping at Bacino's to enjoy a beer on the lawn. (Make sure you go to the Bacino's on Diversey. There is another one on Lincoln Avenue, but if you find you accidentally went there, just do the Lincoln Park itinerary above. You can't lose!) After Bacino's, you can walk next door for some fun at the driving range or mini golf if you want.
Whether you golf or not, two options from Bacino's and the golf range:
1. Walkers can walk east along the pond and under Lake Shore Drive to emerge at the Chevron Sculpture at Diversey Harbor. It's a great place to throw the frisbee, play some music, or just lounge by the water. You can pick up the Lake Front Path from there and either walk south toward the Buddha heads or north toward Belmont Rocks and the AIDS garden. (My vote is north.) If you walk a bit further north from Belmont Rocks, you can pass through the bird sanctuary.
2. Bikers can walk from Bacino's to either of the two nearby Divvy bike stations (one just a minute south, at Lake Shore and Diversey, and one about three minutes north, at Lake Shore and Wellington) and rent some bikes (get the Day Pass and ride the classic Divvy, it's the best bang for your buck) and ride the path north. Stop at the bend after Irving Park Road to take in the peace garden to the left.
Hop back on the bike and ride until you find yourself alongside the shady trees overlooking Lake Michigan. Drop down and enjoy the view. Keep an eye out for the guys with the mobile ice cream carts (and bring some cash just in case). You can dock a Divvy bike at any dock and just continue exploring from there. Whenever you want to head back, just find a nearby Divvy station, grab a bike, and head south toward Lincoln Park. The Divvy Day Pass includes unlimited rides as long as you keep each ride under three hours. (If you are really ambitious and want to break three hours at once, just find a Divvy station and swap bikes. Every time you dock your bike, the clock restarts.)
If you are a runner, just jump on the Path at any convenient point and run until your heart is content. If you want more exercise, the park just west of the Path between Diversey and Barry (where Bacino's is) has several outdoor fitness stations. Hop on and sweat with Chicago. Afterward, walk (or jog, you fitness fiend, you) east through the tunnel and get a refreshing juice or smoothie at the 31 North Oasis stand. What a Sunday you're having. And the wedding hasn't even started yet.
The Loop and nearby areas are the heart of the tourist district. Many of you will be staying in River North just across the river. There's plenty for you to do there.
For first-timers and people who prefer classic tourism, head to the Bean ("Cloud Gate") and walk east to explore Millennium Park, the crown jewel of Chicago's downtown district. You'll find mini golf at Maggie Daley Park, rock climbing, a kind of hedge maze thing, and a serpentine silver bridge to nowhere special. Definitely walk south down Michigan Avenue and splash among the faces at Crown Fountain. Then walk through the garden at the Art Institute. (If you have time, it is absolutely worth going inside to stir up some feelings.)
After the Art Institute, go a block east to Columbus, then walk a block or two south to the farmers' art field. Then walk east down Ida B. Wells Drive to pay your respects to the man who scored four touchdowns to lead Polk High to victory over Andrew Johnson High in the 1966 City Championship.
Finally, the Navy Pier, albeit very famous, is not all the interesting in my estimation, but it hosts very awesome and free fireworks every Saturday night at 10:00, so if you find yourself near the water around that time, find a good spot and enjoy the show.
If you have already seen the big hits (or just aren't interested in them) but want to stay closer to your hotel before the wedding, here are a few more suggestions:
The best of the traditional tourist activities (and a must-do, in my humble estimation) is the architecture boat tour. There are several different companies, but they all offer basically the same tour. Shoreline is popular and favors pop culture tidbits. The Architecture Center's boat tour is excellent and emphasizes history and the architecture itself. My favorite is the Summer of George (Their guides are gold, Jerry. Gold!), but it leaves from much farther south than the others, which all leave from River North, at the ferry terminal on the northwest corner of Michigan Avenue and Wacker. It's at the Wrigley Building, which is beautiful and worth a look on its own.
Grab a seat on the deck of the boat, take in the views, the history, and enjoy the water. All the tour boats have bars and refreshments.
Those of you staying in River North can enjoy a stroll down the Riverwalk. You can enter from the staircases on West Wacker Drive on the south side of the river, right next to any of the bridges connecting River North and the Loop. Get a cold drink at Tiny Tapp and watch the boats go by. If you are there in the evening, be sure to hang around between 9:00 and 9:30, when you can watch Art on the Mart, a 30-minute digital public art display that is projected across the river on to the very ugly but historically interesting Merchandise Mart. It's really cool. (And free!)
Walk to the west end of the Riverwalk and lounge on the grass across from Wolf Point, where the three branches of the Chicago River intersect. If you're there at night, the new apartments over the water make for a positively beautiful view. (Urban ecosystems can be gorgeous too!)
There's plenty to do on the east end of the Riverwalk too, but I never seem to find myself down there. There's a nice little beer garden though, and the Architecture Center is over there.
You can rent some kayaks and paddle the river for a while. It's a lot of fun to slosh around with the boats and see the city enjoying the Riverwalk on a nice summer day.
From the west end of the Riverwalk, you can walk up the stairs at Wacker and Lake and continue south down North Wacker.* Walk down Wacker for about seven minutes to Madison Street and make a right, then cross the bridge over the river. From there, you can catch a ride on the Chicago Water Taxi. Poke around Chinatown Square for a bit, and then grab some lunch at any of the countless restaurants nearby. Take a lap around Chinatown before heading back to the paifang to catch the Water Taxi back north to Madison, or take it all the way to Michigan Avenue and get off in the middle of the throng of tourists. (Michigan Avenue is home of the "Magnificent Mile," which is mostly just a lot of foot traffic and high-end shopping. I'd skip it.)
*-Astute readers will note that I mentioned walking down North Wacker Drive just a few sentences after directing you to West Wacker Drive. The street makes a hard left turn, so there is both a West Wacker and North Wacker, and, in fact, also an East Wacker and a South Wacker. Plus there is also Upper Wacker and Lower Wacker, and, yes, also Lower Lower Wacker. I am serious. Someone thought this was a good plan.
Chicago is famous for jazz and the blues. Stop by Kingston Mines in Lincoln Park or Buddy Guy's in the South Loop to get your fill of tasty licks. The Green Mill in Uptown has excellent jazz and big band music (be warned it's cash-only). Andy's Jazz Club & Restaurant in River North is one of Chicago's best-known and well respected venues, pulling famous acts across the world to its steps.
Pearl Jam did not pass our wedding band audition, but they settled instead for playing Wrigley Field the night before the wedding. The Cubs are out of town (sorry), but Wrigley hosts tours if you want to relive a century of futility.
Second City Theater is a launchpad for comic talent, including Tina Fey, Steve Carell, and Bill Murray, among like a thousand others. Its shows are pretty good, usually. Sometimes. Improvised Shakespeare at the iO Theater is the best improv show in town.
The famous museums at Museum Campus are all solid, but don't overlook the Chicago History Museum in Lincoln Park. It's really great, and it's a lot cheaper and easier to navigate than its more famous counterparts.
You can also spend the day trying to find John Cusack, an endeavor in which Kevin has been unsuccessful despite 12 years of effort. But he can't hide from all of us.
River North and nearby West Loop are brimming with renowned and fancy restaurants about which we know nothing. If you are of that bent, Google is your friend. Here's the stuff we like:
Crisp, at 2940 N. Broadway in Lakeview, is the #1 tastiest fried chicken in the known universe. Get the Seoul Sassy sauce and let it wash over you. (But not literally. That's weird.) If you love or want to try great scotch, walk three minutes south to the very cozy Duke of Perth at 2827 N. Broadway, to enjoy a warm and welcoming atmosphere and a robust scotch selection.
Hot dog stands everywhere! They're really good, I promise. We like Flub a Dub Chub's on Broadway in Lakeview. Chicago's Dog House on Fullerton in Lincoln Park is also good. Wiener's Circle is famous but overrated, but otherwise pretty much any hot dog stand will work as long as it has the Vienna Beef logo.
Au Cheval's burger is tops in town by reputation.
If you want to try deep dish pizza, Pequod's in Lincoln Park is the best in the city. Lou Malnati's is a fixture too. Yes, New Yorkers, we know it's not the same. Pipe down and eat.