With its big city amenities and classic Midwestern charm, Chicago is an excellent vacation spot for families and couples. Enjoy a day exploring the Lake Michigan shoreline, or take in views of the city from the Ferris wheel on the Navy Pier. Catch a Broadway touring production at the Privatebank Theatre, or lose yourself in six floors of shopping at the iconic Macy’s State Street. Book a stay at one of many Chicago vacation rentals today, and enjoy the excitement of the city with the comforts of home. Whether you’re coming for the Magnificent Mile shopping or the spectacular Chicago Marathon, there’s something for everyone in this bustling city. With that said, here are the most unforgettable attractions in Chicago.
1. Gold Coast
If your ideal vacation involves unparalleled luxury, Gold Coast is the place for you. Vacation rentals in this opulent neighborhood place you within minutes of Oak Street, which is home to some of the best high-end shopping in the city. Rent an apartment by the water to experience stunning views over Lake Michigan and immediate access to the popular lakeside running path. After a day of exploring, check out one of the many local Michelin-starred eateries, and experience Chicago nightlife on bustling Rush Street.
2. The Loop
Stay in the middle of the action in The Loop, Chicago’s downtown core. This busy neighborhood places you within a few minutes’ walk of the city’s most popular attractions. Stroll over to Millennium Park to check out the spectacular Cloud Gate, which is more commonly known as “the bean.” From there, watch an outdoor concert at the Jay Pritzker Pavilion, wander through the Lurie Garden and watch the water shows at the Buckingham Fountain. Vacation rentals in this neighborhood tend to be condos and apartments, making it a great choice for couples and small families.
3. Magnificent Mile
Shop until you drop in the Magnificent Mile, a neighborhood that’s famous for its high concentration of stores. From the sprawling Apple store to popular retailers such as H&M and Bloomingdale’s, this area offers something for everyone. The Magnificent Mile comes to life during city events, such as the Lights Festival and the St. Patrick’s Day Parade. Vacation rentals on either side of North Michigan Avenue provide excellent views of the street and fast access to local shops and restaurants.
4. Logan Square
Experience life like a Chicagoan in Logan Square. With its spacious apartments and historic homes, this welcoming neighborhood provides plenty of vacation rental options for families and large groups. Rent a bike to take advantage of the local trails, or enjoy evening walks past beautiful artistic murals. Choose a rental near Logan Square itself for quick access to excellent coffee shops and reasonably priced restaurants, or stay near the Blue Line train for convenient trips downtown.
5. South Loop
Kick back in your ultra-modern high-rise condo in South Loop. Home to a mix of young professionals and established city-dwellers, this upscale neighborhood is replete with stunning apartments and lake views. After business hours, the South Loop streets offer a quiet escape, all just minutes from the bustle of downtown. If museums are your thing, walk a few blocks east of Museum Campus, where you can spend days exploring the Field Museum, Shedd Aquarium, and Adler Planetarium.
6. Hyde Park
You’re never far from green space in Hyde Park, an up-and-coming neighborhood located eight miles south of downtown Chicago. Vacation rentals on the west side border the enormous Washington Park, which provides everything from playgrounds to an aquatic center. Midway Plaisance Park comes alive with runners in the summer and ice skaters in the winter, and Nichols Park welcomes visitors with its community flower garden and extensive walking path. Near the lake, check out the Museum of Science and Industry, or enjoy beautiful water and city views at Promontory Park.
7. Wrigleyville
Experience the thrill of baseball season in Wrigleyville, the home of Wrigley Stadium. Packed with beautiful historic buildings and buzzing nightlife, this fun-loving neighborhood is a great choice for families and couples. Catch a Cubs home game, or simply revel in the energetic atmosphere with an outdoor table at a local restaurant. On the lakeshore, the Sydney R. Marovitz Golf Course offers nine holes with a view of the water, and the nearby Chicago Lakefront Trail offers bike rentals and walking opportunities.
8. Lincoln Park
Luxury meets peace and quiet in Lincoln Park, a lovely neighborhood situated just north of Old Town. Characterized by stunning brick buildings and tree-lined streets, this area is the perfect place to relax after a busy day in the city. Choose a luxury vacation rental on the neighborhood’s namesake park, and enjoy instant access to peaceful strolls and quiet picnics. Choose from a wide variety of restaurants on Clark Street, or bring the kids to Lincoln Park Zoo.
9. River North
Experience the best of city living in River North, a neighborhood packed with restaurants, entertainment options and high-rise apartment buildings. Most vacation rentals in this area lie a block or less from world-class eateries such as the Frontera Grill and the Purple Pig. Check out the condos that line the Chicago River for beautiful morning and evening views, or opt for an east-side rental to be close to the busy Millenium Mile area. After dark, check out the House of Blues or check out the city’s best art galleries near Superior and Huron.
10. Bucktown
If you’re looking for nightlife and youthful energy, look no further than Bucktown. This buzzing, creative neighborhood offers a fascinating blend of vintage shops, stunning street murals, and trendy farm-to-table restaurants. Spend a few days wandering through the galleries and stores on West Armitage Avenue or North Damen Avenue, and don’t miss The 606, a park and trail system built on an old elevated train line. The Blue Line train stops nearby, connecting you easily to downtown or O’Hare Airport.