A weekend is barely enough time to scratch the surface of Chicago's neighborhoods. Still, it will solidify the city among your favorites. When you return, you can pick up where you left off, adding more museums and neighborhoods each visit.
Starting from Friday evening and ending on Monday morning, this itinerary is perfect for anyone planning a weekend getaway.
FRIDAY
When arriving at Chicago's O'Hare airport, opt for the Blue Line train to the city as traffic often makes it faster than a rideshare. Once downtown, change to an Uber for your remaining journey. Consider staying in Chicago's Gold Coast at Hyatt's Thompson or Marriott's Talbott Hotel. After check-in, start sightseeing with one of Chicago's most recommended activities.
Head to the Riverwalk and board Chicago's First Lady for an architectural cruise. This tour will give you a good overview of the city's layout and educate and entertain you with stories about the skyline. Book tickets in advance.
Linger along the Riverwalk for a pre-dinner drink or head early to the Fulton Market district of Chicago's West Loop. Fulton Market is full of great options, but try for a reservation at Rose Mary, where you can enjoy shareable Italian plates. If unable to secure a booking, across the street is Time Out Market. This international food hall boasts 18 concepts so everyone in your group can find food they like.
SATURDAY
The Thompson is a block from Oak Street Beach. Head there in time for sunrise and enjoy the calm among the morning joggers in what will soon be a busy beach scene under Chicago's postcard skyline.
Rent a Divvy Bike and head out on the Lakefront Trail. Start biking north, and on your way back, you'll be rewarded with the quintessential view of Chicago. Pass up your starting point and continue south. You'll pass the Cloud Gate (i.e., The Bean) along the way. Stop if you must, but continue biking to Shedd Aquarium for another excellent view. Divvy bikes can be returned to any station, so you can stop anywhere during your ride. Upon returning to Oak Street Beach, stay awhile and soak up some sun on the shores of Lake Michigan.
Follow all the morning activities with a casual and healthy lunch at Beatrix at 671 N. St. Clair Street.
Beatrix is adjacent to Michigan Avenue, so spend the afternoon shopping. The walk back toward your hotel along Rush Street is also full of great stores.
For dinner tonight, enjoy the lively neighborhood your hotel is in. The surrounding Chicago restaurants have lovely sidewalk patios. Try the crab cakes at Hugo's Frog Bar & Fish House, go next door for fancier fare at Gibsons Bar & Steakhouse.
In the summer, there is almost guaranteed to be a Chicago neighborhood festival with music, food, and other street vendors. Check out the events calendar on the Choose Chicago website to see where to end your day.
SUNDAY
Brunch at The Lunchroom, inside boutique retailer Space 519. Shop for gifts, jewelry, and home goods while you wait for your meal.
After brunch, check out another can't-miss Chicago staple—The Art Institute in Grant Park.
When you're ready to change from art to architecture, walk west up Adams Street to The Rookery and take in the grandeur of this Frank Lloyd Wright-designed lobby hidden in a Chicago office block. Let this whet your appetite for all things, Wright. Chicago has several Wright homes that are great for touring on subsequent visits.
After the lobby, head to Willis Tower to redeem your timed entry tickets to the SkyDeck. Here, you'll head to the 103rd floor for breathtaking city views. You can also step out on The Ledge, a glass floor extending out from the central tower.
For dinner, it's time for one more Gold Coast, genuinely hidden gem, Le Colonial. This Vietnamese restaurant will transport you back in time with its rosewood bar and palm-filled terrace overlooking Oak Street.
MONDAY
Before flying home, squeeze in one more coffee and brunch. La Colombe Coffee is two blocks from The Thompson. Grab a cortado, walk the tree-lined streets, and imagine yourself in one of the beautiful homes. End your walk at 3 Arts Club Café inside the tranquil garden courtyard of Restoration Hardware, where breakfast is served daily.
