Chicago makes a perfect weekend getaway from just about anywhere. Centrally located, it’s New York without the attitude and Los Angeles without the gridlock; a metropolis united by fierce loyalty to its sports franchises – and bitterly divided by which franchise commands that loyalty.
The city is also blessed with a train system called the ‘L’, which is as user-friendly as it is iconic for its appearances in films and TV shows that shoot here. So: where should you let the L to take you if you want to spend the perfect Saturday in Chicago?
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The Palmer House is one of Chicago’s most stunning hotels. Built in the late 1880s, the ceiling, sconces, and beautiful staircase transport you back in time. The hotel has hosted presidents, authors, and entertainers. History aside, the rooms are surprisingly modern and spacious. Located centrally, The Palmer House is an ideal starting point – wherever you want the ‘L’ to take you.
Once you’ve checked in, go sip a cocktail or two 96 floors up at The Signature Lounge, which sits atop the observation deck at the John Hancock Building. Spectacular views of the city are guaranteed, the cocktail menu is extensive, and there are a few food options as well. A drink costs about the same as a ticket to the observation deck, so you’re basically getting the view with a free cocktail… or a cocktail with a free view, whichever works for you. If you want something more substantial to eat, you’ll find The Signature Room, a full restaurant, just one floor below.
To end your evening, make your way just 10 minutes north to see some of the comedy world’s best and brightest! The Second City launched the careers of Alan Alda, Gilda Radner, Jim & John Belushi, Dan Aykroyd, Tina Fey, Stephen Colbert, Steve Carell, John Candy, Chris Farley, Amy Poehler, and many more. They have two shows, at 8 p.m. or 11 p.m. on Fridays. On Saturdays, they have a Best of Show at 4 p.m., in which you can see some of the The Second City’s all-time best sketches, improvisations, and songs.
Start your Saturday with a trip to the West Loop for breakfast at Little Goat Diner. It’s the brainchild of Chef Stephanie Izard, and sister restaurant to her James Beard “Best New Restaurant” nominee Girl & the Goat. It’s much easier to get a reservation at the Diner, especially for breakfast, and the atmosphere is great. It’s one large room of togetherness. Grab a booth, a seat at the bar, or plop down at a long table with strangers who are also there to enjoy the Fat Elvis Waffles or the Ooey Gooey Cinnabuns.
If you want to give back while enjoying brunch, try Inspiration Kitchens. This West Side restaurant employees people who are homeless or are dealing with poverty. The employees are part of a 12-week training program that teaches culinary skills,with the goal of getting them a good job in the field when their training ends. While you get a great meal, you’re also giving someone a leg up to a better life. In addition to brunch on the weekends, they’re open for lunch Wednesday-Friday. You can make a reservation.
Next, head to the Lakefront Trail along Lake Michigan. You can pick up the path on the Museum Campus, near Shedd Aquarium and Adler Planetarium. It will give you one of the best views of the city, and you can walk the path back toward the Chicago River. If you want to visit Shedd Aquarium, Adler Planetarium, or the Field Museum of Natural History, this is the perfect opportunity.
Being popular with families, Shedd can get crowded. The oceanarium, which looks out onto Lake Michigan, is home to beluga whales, dolphins, sea otters, and sea lions. You can relive NASA’s mission to the moon at Adler, the oldest planetarium in the country. The star of the show at the Field Museum is Sue, the largest T. Rex ever discovered. There are a wide range of exhibits, including a room filled with rare jewels! If you’re going to visit several of the museums, consider getting the City Pass. It may be worth purchasing, depending on how much you plan to see during your stay.
A great outdoor option is the Architecture River Cruise. It’s a spectacular way to learn about Chicago’s buildings and history. The Chicago Architecture Foundation partners with First Lady Cruises for the tour; you know it’s good when even locals rave about it. It’s consistently rated one of the top tours in the entire country, not just the city. Before you board, try and pick out the corn cobs of Chicago architecture. Hint: you can see cars parked at the bottom! After your 1.5-hour tour, you won’t look at those two buildings, or many of the others, the same again.
You’re surely hungry, and if you enjoyed The Second City on Friday night, you’ll want to have lunch in the spot that Second City Alums made famous on Saturday Night Live, the Billy Goat Tavern. Order a Cheezborger and Cheeps and imagine Belushi, Murray, and Aykroyd performing the sketch. (The restaurant was a known hangout for journalists with the Sun Times and Tribune offices close by, but it was also frequented by Belushi and Murray.) It’s on lower Michigan, beneath Michigan Avenue. You can get there by going down the stairs in front of 430 North Michigan Avenue. You’ll think you’re in the wrong place and that’s when you’ll see it.
Upper Michigan Avenue is known as Chicago’s Magnificent Mile. If you’re a super shopper, or are traveling with one, you’ll want to spend some time here. You’ll find everything from Under Armour to Burberry. At the north end of Michigan Avenue, you’ll find some of the most exclusive shopping in Chicago on Oak Street. Escada, Harry Winston, and Dolce & Gabbana are among the high-end boutiques you may want to browse.
It’s hard to pass up a game at Wrigley Field if the Cubs are in town while you’re in the Windy City. Built in 1914, it’s the second oldest ballpark in the country, and it’s recently undergone some renovations. This could alter your afternoon or evening plans. If it’s not baseball season, or if the team is out of town, they do offer tours. It’s a fun place to see a game from the seats or the bleachers. Before or after the game, grab a beer at Murphy’s Bleachers to complete the experience. If you don’t care about baseball or the history of it, carry on with shopping and sightseeing.
Chicago is home to many fantastic restaurants, run by some of the most well-known chefs in the country. Grant Achatz, Rick Bayless, Beverly Kim, Tony Mantuano, and Paul Kahan all have restaurants here. Each of these chefs offer fantastic options. Achatz’s Alinea is one of Chicago’s two Michelin 3-star restaurants. It’s very expensive, but one of the ultimate culinary experiences in the country. This may go without saying, but reservations are required.
If you want something traditional, try dinner at Gibson’s Bar & Steakhouse or the city’s oldest steakhouse, Gene and Georgetti. Frank Sinatra, Bob Hope, and Lucille Ball all stepped through the doors, which opened in 1941. Chicago’s steakhouses cut their steaks thick, and the sides are a la carte. It’s a mid-century experience you won’t regret.
Stepping back to the mid-1900s may not be far enough, so make sure to get a taste of 1920s Chicago. The city embraces its prohibition era history with several speakeasys around the city. Some are easier to get into than others. Watershed has its own website, so it’s probably not too secret, but it evokes that hush-hush feeling without requiring a password to get in. The cocktail list is extensive, and there are small bites if you’re hungry. Watershed is located below Pops for Champagne in River North, so if you just want a glass of bubbly to end the evening, you’re in the perfect spot that that as well!