12 Stunning Chicago Vacation Rentals for a Lively Windy City Stay

Ditch the boring stay in a hotel and opt instead for a relaxing and luxurious vacation rental in Chicago.

Chicago is a historic city with a lot of personality. Chicagoans are famous for their love of baseball, Chicago-style hot dogs, and deep-dish pizza. The city is also home to iconic architecture that includes the dreamy Cloud Gate and the sky-high Willis Tower. Not to mention the peaceful waters of Lake Michigan and the Chicago River that add a nice touch of nature to the concrete streets.

America’s third-largest city sees an astounding 55+ million tourists each year, meaning there are plenty of lodging options to choose from. Cut through the clutter of subpar hotels and elevate your stay with one of the best vacation rentals in Chicago.

Related Read: 10 Best Weekend Road Trips From Chicago, Illinois

1. Luxury Loyola 3 Bed

Why you should stay: A homey two-story walk up in a prime location to Loyola University, the subway, and the beach.

• Sleeps: 6
• Minimum stay: 2 nights
• Rates start from: $214/night

For a quiet stay not far from the lake, this luxury Loyola 3 bed is an excellent choice. This three-bedroom apartment is in the Rogers Park neighborhood, an area of Chicago close to the Hartigan Beach Park and Loyola campus. This family-friendly home is stocked with kid essentials like a high chair and child-safe kitchenware for those traveling with young ones.

Other impressive amenities include a large front balcony, a heated enclosed back porch, and onsite laundry. The red line is just down the road for convenient access to the rest of the city. If you’re traveling by car, the hosts have street parking permits on hand for your stay.

2. Wrigley Loft

Why you should stay: A spacious city condo in the heart of Wrigleyville featuring a rooftop patio overlooking the Chicago skyline.

• Sleeps: 14
• Minimum stay: 2-4 nights
• Rates start from: $687/night

An open floor plan and tall ceilings create a cozy atmosphere at the Wrigley loft, a two-story, 2,000-square-foot apartment in Wrigleyville. This Chicago VRBO is an ideal getaway for large groups with its three bedrooms, pull-out sofa sleeper, and additional queen air mattresses. Your group is sure to have a blast in the game loft that’s stocked with board games, arcade games, and a foosball table.

The real star of this home is the rooftop patio. At the top of the apartment, sit back and take in majestic city views. There’s also a back porch set up with a grill for family cookouts. This property is a few blocks from Wrigley Field and a short walk to paths along the lakefront.

Related Read: 9 Delightful Weekend Road Trips From Columbus, Ohio

3. Chicago Brick Home

Why you should stay: Enjoy a high-end and entirely private home just two miles from the Magnificent Mile.

• Sleeps: 12
• Minimum stay: 3 nights
• Rates start from: $618/night

Contemporary decor and high-end finishes make this Chicago brick home special. The lower level is furnished with a kitchenette, a bedroom, and a bathroom offering a second private living space. There is also a gourmet kitchen, an expansive living room with a fireplace, and a top-floor master suite on the upper levels.

The home has a fenced-in, well-manicured yard as well as two balconies and a porch connected by a spiral staircase. Enjoy sitting out on the outdoor areas furnished with plush patio seating and a barbeque grill. This beautiful Chicago vacation rental is in Noble Square, a quiet area with a family-friendly park.

Related Read: 10 Romantic Getaways Near Chicago, Illinois

4. Fulton Market Penthouse

Why you should stay: A stylish penthouse with industrial vibes tucked away in the heart of one of Chicago’s liveliest neighborhoods.

• Sleeps: 12
• Minimum stay: 2 nights
• Rates start from: $775/night

If modern and unique lodging is your speed, the Fulton Market penthouse checks all the boxes. Located in Chicago’s old warehouse district, the West Loop is a fantastic place to stay for highly-rated dining and nightlife.

The interior of this apartment embodies Chicago’s industrial era. As you walk inside, the exposed brick walls, sliding steel door, and exposed wooden beams catch your eye. The large living room has wide windows that let natural light pour in and look out onto Fulton Market. This VRBO is a one-minute walk from the Morgan train stop and ten minutes from the main strip.

Related Read: 10 Exciting Weekend Road Trips From Indianapolis, Indiana

5. Sunny Apartment

Why you should stay: Experience a classic Chicago brick apartment in the quiet yet vibrant Lakeview district a short walk to Wrigley Field.

• Sleeps: 5
• Minimum stay: 2 nights
• Rates start from: $156/night

This sunny apartment is a two-bedroom Airbnb Plus with classic hardwood floors and modern decor. The interior maintains the original charm of days gone by in the exposed brick, wooden window casings, and idyllic ivy that grows up the exterior walls.

The apartment also features a wood-burning fireplace, a work desk, and a second-story balcony with seating. Wrigley Field, the lakefront, and the Graceland Arboretum are all close by. The surrounding neighborhood is also known for its hip bars, cafes, and restaurants.

6. Penthouse #1

Why you should stay: Wake up 55 stories above the city in this glamorous penthouse with an expansive balcony and epic downtown Chicago views.

• Sleeps: 8
• Minimum stay: 3-4 nights
• Rates start from: $867/night

Indulge in the high-end Penthouse #1 in Chicago’s posh River North neighborhood where high rises and luxe eateries amaze. Not only is the surrounding community incredible, but so is the interior of this three-bedroom condo. Tall windows and 20-foot ceilings make this already spacious home feel big and inviting.

The building also features a community swimming pool, fitness room, and grilling area. Top Chicago attractions like Millennium Park are less than a mile away, and the red line is across the street, taking you to the most popular places around the city.

Related Read: 9 Fabulously Unique Places to Stay in Illinois

7. Corner 3BR Loft

Why you should stay: Sleep close to the fun atmosphere of Fulton Market where cocktails and Chicago’s Theater Loop are just around the corner.

• Sleeps: 12
• Minimum stay: 2 nights
• Rates start from: $751/night

This corner 3BR loft is a classic brick-and-timber building that’s been recently updated with modern amenities. The home features wide-open living spaces with exposed brick, wooden beams, and numerous windows that brighten the place. Enjoy the Fulton Market views from the comfort of the living room or head down and sip cocktails in the courtyard just outside the front door.

This spacious apartment features three bedrooms with enough sleeping space to accommodate large groups. The property does not have parking available, but it’s near Chicago’s green and pink metro lines for easy transport around the city.

8. Heart in Lincoln Park

Why you should stay: A pleasant vacation rental with thoughtful touches in the city’s affluent Lincoln Park.

• Sleeps: 6
• Minimum stay: 2 nights
• Rates start from: $287/night

Heart in Lincoln Park is a cozy home located just a five-minute walk to the Lincoln Park Zoo and an easy 30-minute drive from the Chicago O’Hare International Airport. The neighborhood rocks a high walkability score, making it super convenient to find quality places to eat, shop, and have fun on foot.

This Chicago Airbnb offers guests onsite secured parking, a rare find in the city. The home also has free laundry machines, two bedrooms and a sofa sleeper, and an indoor fireplace for toasty evenings in. Guests also adore the impeccable cleanliness and homey touches found throughout the home.

9. Chicago Mansion

Why you should stay: A massive nine-bedroom home named as one of the best rentals in Chicago near Uptown.

• Sleeps: 21
• Minimum stay: 2 nights
• Rates start from: $1,000/night

Treat yourself to this beautiful Chicago mansion nestled in one of the city’s liveliest neighborhoods. This Uptown property puts guests in close proximity to popular jazz lounges, the Lake Michigan coast, and the Uptown Theatre.

The mansion’s interior boasts ornate furnishings, a stunning grand staircase, and a whopping nine bedrooms. In the kitchen, you’ll find espresso coffee machines and a lovely breakfast nook. There is also a spacious fenced-in yard with a fire pit and gated parking available for up to five cars.

10. Andersonville Guesthouse

Why you should stay: A welcoming three-bedroom in a quaint neighborhood known for Clark Street shopping, historic row houses, and a dynamic bar scene.

• Sleeps: 7
• Minimum stay: 2-4 nights
• Rates start from: $518/night

The Andersonville Guesthouse is a home-away-from-home three-bedroom with hotel-like amenities. The bathrooms have been outfitted with high-end touches like a steam shower and a jetted bathtub. Guests have full access to the building’s shared fitness room and incredible rooftop deck.

On the roof, plush seating, cafe tables, and a wooden pergola with string lights foster a magical atmosphere. The unit also has a private balcony furnished with a gas grill and seating. Top attractions like McCormick Place and Montrose Beach are nearby.

11. Loft606

Why you should stay: An extravagant sunny loft boasting over 5,300 square feet of space with jaw-dropping amenities perfect for large groups or events.

• Sleeps: 30
• Minimum stay: 2 nights
• Rates start from: $1,371/night

Loft606 was made to host boisterous and exciting stays. This expansive loft exudes industrial charm through its 26-foot tall timber ceilings, concrete floors, and exposed brick walls. To reach the master suite, you must climb a spiral staircase in what was once a brick smokestack. At the top, the master bedroom features a luxurious bathroom with a rain shower and a jetted tub.

Other incredible touches include a disco ball, a huge glittering chandelier, and a full-sized bar. The hosts allow pets for an additional fee, and special services are also available for booking. Popular Chicago landmarks like Navy Pier and the United Center can be reached via subway.

12. River North Apartment

Why you should stay: An elegant vacation rental with two private units furnished with designer furniture and art.

• Sleeps: 2
• Minimum stay: 3 nights
• Rates start from: $200/night

This River North apartment offers an elevated stay just north of The Loop, Chicago’s bustling downtown area where high rises, the Willis Tower, and the Bean are clustered. The apartment is complete with exposed brick, beamed ceilings, and a sleek modernist design.

If you’ve ever wanted to feel what it’s like to live in a big city apartment, this is your chance. Plus, it’s walking distance to tons of attractions like Navy Pier, Michigan Ave., and the theater district. 

Explore More in the Midwest

Sign up for Weekend Wanderer to join thousands of readers getting epic travel and gear ideas every week.