Ashley & Bobby
Things To Do
Millennium Park
The obligatory must-see that's actually worth it. Take a photo with the Bean, catch some music at the Pritzker Pavilion, watch the kids splash around in Crown Fountain. The big old building across the street at Michigan and Randolph is the Chicago Cultural Center, with free art exhibits and two gorgeous stained glass domes. Grant Park, the larger park surrounding Millennium to the south and east, is less populated with tourists, if you want to see more of the public Lakefront that Daniel Burnham thankfully affirmed "by right belongs to the people."
The Art Institute of Chicago
One of the largest art museums in the world, the Art Institute is full of world-famous by works legendary artists, including Georges Seurat, Pablo Picasso, Edward Hopper, Grant Wood, Chagall, O'Keefe, and the largest Impressionist collection outside Paris. The two bronze lion statues outside the main entrance are often decorated for holidays or in support of local sports teams.
Chicago Architecture Foundation
Chicago has some of the most significant and impressive urban architecture in the world, and the Chicago Architecture Foundation has a myriad of tours to show it all off. The boat cruises are an incredible introduction and experience, but the walking tours are cheaper and just as impressive. The gift shop at their headquarters has lots of great stuff too.
Shedd Aquarium
The Shedd is one of the largest indoor aquariums in the world, with tanks containing 5 million gallons of water. Featuring beluga whales, dolphins, sea otters, penguins, sea lions and more, it's a must for anyone who loves sea creatures. But know that it's more expensive than the other museums and can get very crowded
The Second City
One of the most famous and prolific comedy theatres in the world, Second City has live shows every night of the week on a number of different stages in Old Town. The walls of the stairwell and lobby are lined with faces you know from TV and the movies who got there start here.
Oak Street Beach
There are a dozen beaches up and down the lakefront, but Oak Street is right in the shadow of the skyline and close to everything downtown. Where else can you be sunning on a gorgeous beach one minute and dining at a world class restaurant the next?
Lincoln Park Zoo
A 35-acre zoo in the heart of Lincoln Park with free admission and includes monkeys, apes, zebras wolves, penguins, lions, tigers and bears (oh my). Perfect to stroll through as part of a longer walk in the park. The bridge between the Zoo and South Pond has a lovely view south of skyline.
Jackson Park
A 500-acre masterpiece designed by Frederick Law Olmstead, Jackson Park was the site of the 1893 World's Columbian Exposition. The Museum of Science and Industry at the northern edge of the park is the only building remaining from that time (it was the Fair's Palace of Fine Arts). Take a walk around the Wooded Isle at the center of the park and enjoy the beautiful surroundings. The southwest corner of the park is the future site of the Barack Obama Presidential Library.
Lou Malnati's Pizzeria
Go to Pizzeria Uno or Due if you're looking for history or kitsch. But if you're looking for the best tasting deep dish pizza, you'll find it at Lou Malnati's. They have many locations around the city, this is just the downtown location that's more nicely decorated. And to be clear, we don't eat this all the time. In fact, we probably haven't had it since the last time one of you visited.
Portillo's Hot Dogs
The other renowned Chicago food: the hot dog. Portillo's is a fun and delicious place to treat yourself to our fast food legacy. There's not supposed to be ketchup on it, we think. We don't know. We don't eat them. Bobby recommends the Italian Beef sandwich instead, another classic. Ashley likes the cheese fries.
Rosa's Lounge
A gritty and intimate place to hear outstanding blues music live, Tuesday-Saturday nights. There are other blues clubs less remote than this one on the fringes of Logan Square, but the musicianship on display here makes it well worth the journey.
Kingston Mines
A more party and dance focused blues club in Lincoln Park with music 7 nights a week on two stages as well as a menu of BBQ favorites.
Music Box Theatre
A historic and ornate movie theater from the 1920s which shows classic, indie and foreign films daily. A live organist plays between showings sometimes, just like the old days.
The Green Mill
A classic cocktail lounge that opened in 1907 and was a favorite of Al Capone's. There's a picture with his face on it at the booth he used to sit at. The bar features live jazz nightly and the Paper Machete "live magazine" show on Saturdays at 3pm.
Half Acre Beer Co Balmoral Tap Room & Garden
Chicago has literally dozens of craft breweries and so many are excellent: Revolution, Begyle, Dovetail, Moody Tongue, Off Color, Pipeworks, Metropolitan, Whiner. But Half Acre is our favorite and their new facility on Balmoral with outdoor seating is perfect for a cold one on a Summer day. Spiteful Brewing right next door is another favorite worth a stop.
Hopleaf
A beer lover's paradise, Hopleaf has been pouring Belgian and American brews for over 25 years, predating the craft beer explosion. With 68 taps and an incredible menu of Belgian fare—the mussels and frites are legendary—it's worth the trek north. Strictly 21+ so don't bring the kids. The Andersonville neighborhood has a Swedish background, and if you stroll north up Clark from Hopleaf, you'll see some restaurants, shops and a museum all clad in yellow and blue.
Maria's Packaged Goods and Community Bar
Bridgeport has been a stronghold of political power for decades (see Daley, Richard J. & Richard M.) so it's only fitting the neighborhood also be home to another Chicago classic: the packaged good store (or slashie, as the hipsters call it). Walk into Maria's front entrance and it looks like a small vintage liquor store. Head further back and you'll see it's an honest-to-goodness tavern too. Kimski, the kitchen next door which can be accessed through the bar too, serves up amazing Korean/Polish food.
The Violet Hour
The leader of the cocktail revival movement in Chicago, Violet Hour serves up some of the best drinks anywhere. The entrance is a non-descript door with no sign on Damen Ave just south of the Blue Line, and be sure to read the rules before you go: "No cell phone use inside lounge. Proper attire requested. Please, no baseball hats. Sorry, no reservations. ... No O-bombs. No Jager-bombs. No bombs of any kind. No Budweiser. No light beer. No Grey Goose. No cosmopolitans. And finally, please do not bring anyone to The Violet Hour that you wouldn’t bring to your mother’s house for Sunday dinner."
Longman & Eagle
If you're looking for food more elevated than deep dish or hot dogs, Chicago is a foodie heaven. The Logan Square neighborhood has many excellent restaurants, and Longman & Eagle is one of our absolute favorites. It's a Michelin-starred farm-to-table gastropub with a constantly changing menu and over 400 whiskey labels.
Gene's Sausage Shop and Delicatessen
At the heart of Lincoln Square, the historical home of Chicago's large German population, is Gene's Sausage Shop. The first two floors feature a butcher counter and deli, along with a large collection of European beverages, foodstuffs and sweets. But the real draw is the rooftop beer garden. It's the perfect place to soak up the summer sunshine with a pint and a brat. FYI, the rooftop is cash only.
Carnitas Uruapan Restaurant
Pilsen is the heart of the sizeable Mexican community in Chicago. Grab a pound of carnitas and some tortillas from the amazing Carnitas Uruapan and eat lunch in nearby Harrison Park. Afterwards, check out the incredible National Museum of Mexican Art (free admission!) and the murals at the 18th Street Pink Line Station.
Calumet Fisheries
For those looking to get off the beaten path, check out this classic seafood shack that serves all sorts of seafood either smoked or fried. It won an America's Classics award from the James Beard Foundation, and is right next to the 95th Street Bridge, which was featured in The Blues Brothers film.
Chicago Botanic Garden
Twenty miles north of downtown, the Chicago Botanic Garden is an oasis of horticultural beauty. Japanese gardens, bonsai trees, English walled gardens, greenhouses and a prairie: it's 385 acres of stunning landscapes that will make you forget the city entirely. An easy drive up the Edens Expressway, or you can take the UP-North commuter rail which will let you wave at Writers Theatre on the way there.