Experience big-city vibes in the heart of the Midwest.
Chicago will slam-dunk your expectations, whether you’re traveling with children or looking for a culture-and-cocktails vibe. Stay downtown to surround yourself with the iconic skyline, originally built to mark one of the wealthiest cities in the country. For a slower pace, visit the outlying neighborhoods for some next-level antiquing. You can get a little bit of anything and everything in Chicago, making it a great stop no matter whom you’re traveling with.
- The Loop
- Streeterville & Navy Pier
- River North
- Old Town
- Wicker Park
- Logan Square
The Loop is known for its luxury shopping along Michigan Avenue, as well as the ever-popular Millennium Park (home to that selfie favorite, the reflective Cloud Gate sculpture). This neighborhood also offers museums and walking paths with river views, for when you need a break from the crowds.
Shopping, Dining, Theaters
Streeterville & Navy Pier
Bookended by the Magnificent Mile’s iconic stretch of shops and architecture and Navy Pier’s whirling rides and lakefront restaurants, this neighborhood is high on most visitors’ must-see lists. Amid the designer brands and soaring skyscrapers, it’s also a launching point for enjoying Lake Michigan, from swimming at Ohio Street Beach to sightseeing and architecture cruises.
Shopping, Architecture, Beaches, Entertainment
While Chicago has plenty of great nightlife, River North is the place to go downtown when you aren’t quite sure what kind of fun you’re after. From a steampunk-themed barcade (that’s a bar with an arcade) and bowling with cocktails to live music at the House of Blues and a zombie-themed taco counter, you’ve got a ton of options.
Shopping, Dining, Nightlife
While baseball is the main attraction in this neighborhood, there's more to Wrigleyville than home runs and strikes. Theaters, parks and, yes, plenty of sports bars offer up prime people-watching opportunities.
Baseball, Live Music, Bars
While the Victorian-era houses are a huge draw for architecture buffs, Old Town is also home to one of comedy’s most famous clubs: the Second City. There’s a great mix of eateries, boutiques, coffee shops and throwback pubs to help round out your visit.
Architecture, Dining, Comedy, Shopping
One of the hippest neighborhoods in Chicago, Wicker Park packs trendy restaurants and bistros into the spaces surrounding the area’s namesake green space. Today, there are residents of all backgrounds, but this region was historically home to the city’s Polish community.
Nightlife, Dining, Live Music
You can't walk far in Logan Square without smelling something delicious. The neighborhood has a strong Latino community and is home to must-visit panaderías alongside popular parks and cultural centers.
Restaurants, Bars, Cafes, Craft Beer
This neighborhood has deep Swedish roots, which are front and center in its many bakeries and quaint row houses. Andersonville's main drag, Clark Street, is lined with unconventional shops, restaurants and bars.
Architecture, Antiquing, Cafes, Furniture Shops
Stay in The Center of it All
Immerse yourself in your destination at these centrally located hotels.
Plan a Culture Lover’s Weekend in Chicago, Illinois
Take in the Iconic Sites of Millennium Park
Dedicate the day to taking in the iconic Chicago sights and shops in and around Millennium Park, followed by the city’s beloved architecture boat tour.
Sip and Shop in Wicker Park
Visit the trendy boutiques, stop in artisanal bakeries and catch dinner and a show in Chicago’s hippest neighborhood, Wicker Park.
Check Out Magnificent Mile and Navy Pier
Soak in the big-city vibes with a stroll down Magnificent Mile, then have some fun on the must-visit Navy Pier.