In case you need some inspiration when deciding what to do in Chicago, here are a few of our favorites!
Millenium Park & Cloud Gate
While lots of visitors come to see "The Bean," there's a lot more to see at Millenium Park including giant screens of people spitting on you (yes, that's a real thing), the Lurie Garden and Pritzker Pavillion. And while you're there, it might also be a good time to cross the street and check out Maggie Daley Park.
Maggie Daley Park
This park just opened a few years ago, and is a must-see for kids with a large portion of it dedicated to play areas for children. While the ice skating ribbon is popular in the winter, there are also rock climbing walls and tennis courts to keep you busy in the summer months.
Grant Park & Buckingham Fountain
Stretching from just south of Navy Pier all the way to Museum Campus, don't be surprised to see one or two events going on at any given time. If you're staying anywhere in the loop and looking for some exercise, you won't be alone walking or jogging around the park at any time of day either. And don't forget to check out Buckingham Fountain as well, another iconic Chicago landmark.
River Cruise Architecture Tour
Another must-do for anyone visiting Chicago! Enjoy views of the city's sky scrapers and learning about the Chicago history while cruising down the Chicago River. There are a few different companies that offer architecture cruises, but our favorite is the one run by the Chicago Architecture Foundation on Chicago's First Lady.
Navy Pier
Yes, the reception on Sunday is going to be at the Navy Pier Ballroom, but there's so much more to do here! Memorial day weekend just happens to be the grand opening of the new-and-improved Ferris Wheel celebrating the pier's 100th anniversary. For the kids, there are rides, games, laser tag, a children's museum and more.
Magnificent Mile
If your idea of a good time is shopping 'til you drop, then this is the place for you. Starting at the river and running all the way down Michigan Avenue until Oak Street is almost every store you could imagine. The John Hancock building also sits on the north end of Michigan Avenue, if you need a break from spending all that dough. Keep an eye out for the original water tower, which is one of only a few structures in the city that survived the Great Chicago Fire.
Lincoln Park (and Zoo)
While not really walking distance from the Loop, if you make it out to Linoln Park (a short uber-ride away) you won't be disappointed. Lincoln Park is a beautiful place for a walk or run, highlighted by the zoo, which sits in the center of the park and is free to the public. Check out the monkeys, tigers, giraffes and more!
John Hancock Center
The fourth tallest building in Chicago, there are a few restaurants and stores on the ground level, but the real sights to see are on 94th floor at the 360˚ Chicago observation deck where, you guessed it, you can get a 360 degree view of the city. And, for those that need a little more exictement in their life, you can check out Tilt, which will lean you out the base of the building 30 degrees to see eveything straight to the bottom. For those less adventurous, grab a drink at the Signature Lounge on the 96th floor or a bite at the Signature Room on the 95th floor. Time it right and you'll get a fantastic view of the sunset.
Willis Tower
Even though all the cool kids still call it Sears Tower, it's new name doesn't change the fact that it's still the tallest building in Chicago. Similar to the John Hancock, The Sky Deck on the 103rd floor of Willis Tower also gives a 360 degree view of the city from the southern part of the Loop. The Ledge in the Sky Deck takes Tilt one step further and actually puts you in a glass balcony, letting you stare straight past your feet to the sidewalk below.
The Second City
Don't let the name fool you - The Second City is a legendary improv and comedy club that's been the starting point for some of the world's greatest comedians, both past and present. Many of your favorite Saturday Night Live comedians originated here. You can catch a stand-up comedy show or watch one of the many improv shows they put on throught the week.
Deep Dish Pizza
This is what Chicago is known for. The classic debate is between Giordano's and Lou Malnati's (we both prefer Giordano's), so if you're looking to start your deep dish adventure somewhere, we'd suggest one of those two. There are multiple locations throughout the city.
Italian Beef
Another Chicago staple. When staying in Chicago for the first time, a visit to Portillo's is almost required just to experience the fast-food/amusement park atmosphere inside. For something less touristy, hit up any of the Al's Beef locations in the city. While the establishments are typically not much to look at, a beef dipped with hot and sweet peppers will make you think you're in sandwich heaven.
Steakhouses
If you want a steak, you've come to thr right town. From national chains to Chicago-only classics, there's almost too many to choose from. For something that you can't find outside of Chicago, we recommend Chicago Cut Steakhouse, where you might find yourself sitting next to celebrities (Obama eats here every time he's in town!) while overlooking the Chicago River. For a good steak in a not-so-traditional, speakeasy setting, try Bavette's Bar and Boeuf.
Eataly
It's like Italy but with "eat" at the front, get it?! Jokes aside, the grocery store/food court/restaurant is like walking into a mini outdoor market. Each restaurant in the building is set up along the same aisles that hold the food used to prepare your meals. Come for the amazing pasta and pizza, stay for the gelato and Nutella Bar. Be warned, Eataly does get crowded on the weekends.
Xoco, Tompolobampo, Frontera Grill
Rick Bayless has redefined Mexican cuisine in Chicago and around the country. These are his signature three restaurants. Xoco is a casual lunch spot where you can pick a torta (sandwich). Frontera Grill takes a limited number of reservations, but is mostly first come, first served, so plan on coming an hour or so before you want to eat. Tompolobampo is a fancier, sit-down meal and typically requires reservations unless you show up at 4:30 with the hopes of getting one of the walk in tables.
Girl and the Goat & Little Goat
Girl and the Goat is the restaurant that Stephanie Izard opened after winning Top Chef Season Four and serves an eclectic menu, including a section dedicated to, you guessed it, goat. Reservations are hard to come by, but you might be able to snag a table at the bar area if you show up around 4:30pm or 10:00pm. But whatever you do, make sure you get the green beans! If you want something a little less high maintenance, she also owns a newer diner-style restaurant right across the street called Little Goat as well as a brand new Chinese restaurant down the street called Duck Duck Goat.
Au Cheval
The restaurant is dimly lit and typically cramped with music blaring from the speakers. They don't take reservations and you'll probably end up waiitng at least an hour and a half for a table. BUT if you can stomach all those things, get the double cheeseburger with bacon, an egg and (if you're daring) foie gras. That's the one that's been called the best burger in America.
Brunch/Coffee description:| Craving eggs and coffee? There are more options than we have time to offer! A famous choice, with several locations around the city, is Yolk, but you'll end up waiting for an hour on a Saturday or Sunday morning. For a traditional brunch without the wait, try Eggy's. Tucked away in the heart of Lakeshore East, this place is in our backyard and we're likely there on any given Sunday (try the chilaquiles!). For a meatier brunch, try The Publican in West Loop - they're known for their thick-cut bacon. Want both savory and sweet? Check out Cafe Ba-Ba-Reeba in Lincoln Park. A well-known tapas place, they also secretly serve brunch with tapas-sized portions that allow you to order eggs AND pancakes. For a quick cup of coffee, try Intelligentsia (also served at many brunch spots) or Dollop Cafe.
Situated a little further away from the action of the weekend in Wicker Park, if you make the treck out on the Blue Line, you'll be rewarded with margaritas, cold beers and some of the best tacos in the city. If the weather is nice, you can enjoy all this and more while sitting on their huge patio.
Rooftops
When the weather cooperates, everyone in the city heads straight to the roofs. Check out the Roof at the Wit if you're looking for a sheek, ultra-lounge feel. The IO Lounge at the Godfrey lets you hedge your bets as far as weather is concerend with an outdoor and indoor area. Cindy's on the roof of the Chicago Athletic Association Hotel on Michigan Avenue serves great drinks and has a great view of Grant Park, Lake Michigan and beyond.
Pops for Champagne & Watershed
We're celebrating a wedding, why not have some champagne? Pops serves champagne, sparkling wine and cocktails featuring them both. If that's not your fancy, look for the black W and head downstairs to somewhat-hidden Watershed, which features comfy seats, a sizable local beer selection, and some of the best whiskeys around.
Hubbard Street
Just north of the loop across the Chicago River is where you'll find the bars and clubs of the River North neighborhood on and around Hubbard Street. Combined with the slew of restaurants in and around River North, you can easily make a night of wandering the scene here. Social 25 and Rockit are centrally located and good if you're looking for some drinks and dancing, but you can generally find both at most places on Hubbard Street as well. Lines got you down? Try Mercer 311 (usually no line, no cover, and great music).
Breweries
Goose Island is a Chicago staple and has a new tasting room in West Loop that also offers tours of it's facilities. Goose Island also offers a full-service restaurant that serves up its famous brews, for those of you worried about bringing children to a tasting room. Revolution Brewery is also a local favorite and has a tap room and brewery tours a little further from downtown. Lagunitas recently opened a huge brewery in Chicago as well that features an equally huge taproom.
The Aviary
From the same people who operate Alinea, which has been named best restaurant in the country, The Aviary serves creatively designed cocktails that will likely have you telling stories about the drinks you experienced there. They do take a few walk-ins, but your best bet is to buy tickets ahead of time, which is effectively a deposit toward your drinks and snacks for the night.
To help you get oriented, most of the above places are marked below.