List Map

Grand Boulevard Vacation Rentals & NearbyHoliday Homes

Find Vacation Rentals in or near Grand Boulevard. Find vacation rentals in Grand Boulevard, Chicago.

From US $250

Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena

8.9 (194 Reviews) Apartment

The entire place is yours • 60 m² size • Kitchen

Chicago Near South Side • In Grand Boulevard · 4.6km to center

Best Price Match

View Availability

From US $160

Forrestville Ave Large Suite

8.6 (103 Reviews) Apartment

The entire place is yours • 130 m² size • Free parking

Chicago Grand Boulevard • In Grand Boulevard · 414m to center

Best Price Match

View Availability

From US $266

The Penthouse, Lux stay near Downtown, UofC & Lake

9.2 (37 Reviews) Apartment

The entire place is yours • 135 m² size • Kitchen

Chicago Kenwood • In Grand Boulevard · 1.7km to center

Best Price Match

View Availability

a living room with a green couch and a table at Chicago 2BR Suite Perfect for Convention and Business Trips Near McCormick Place, Arena, Soldier Field and Grant Park in Chicago

From US $167

Chicago 2BR Suite Perfect for Convention and Business Trips Near McCormick Place, Arena, Soldier Field and Grant Park

8.6 (31 Reviews) Apartment

The entire place is yours • 88 m² size • Kitchen

Chicago Near South Side • In Grand Boulevard · 4.7km to center

Best Price Match

View Availability

From US $153

South Loop 2BR Getaway with Smart TVs & Optional Parking Near McCormick Place, Museum Campus & Downtown

8.2 (17 Reviews) Apartment

The entire place is yours • 79 m² size • Kitchen

Chicago Near South Side • In Grand Boulevard · 4.7km to center

Best Price Match

View Availability

From US $145

Modern 2BR in South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail

8.0 (35 Reviews) Apartment

The entire place is yours • 88 m² size • Private parking

Chicago Near South Side • In Grand Boulevard · 4.6km to center

Best Price Match

View Availability

a couch and chair on a balcony with a view of the city at McCormick Place 3BR Luxury Penthouse Duplex with Personal Rooftop and Optional Parking for 8 guests in Chicago South Loop in Chicago

From US $245

McCormick Place 3BR Luxury Penthouse Duplex with Personal Rooftop and Optional Parking for 8 guests in Chicago South Loop

9.7 (7 Reviews) Apartment

The entire place is yours • 220 m² size • Private parking

Chicago Near South Side • In Grand Boulevard · 4.7km to center

Best Price Match

View Availability

a living room with a green couch and two chairs at Spacious 2BR Vacation Rental with City View, Optional Parking and Gym Near McCormick Place & Downtown Chicago Attractions in Chicago

From US $145

Spacious 2BR Vacation Rental with City View, Optional Parking and Gym Near McCormick Place & Downtown Chicago Attractions

8.2 (16 Reviews) Apartment

The entire place is yours • 88 m² size • Private parking

Chicago Near South Side • In Grand Boulevard · 4.7km to center

Best Price Match

View Availability

a living room with a blue couch and two chairs at Convenient 2BR Suite in Prime Location with Gym Access & Optional Parking Near McCormick Place and Soldier Field in Chicago

From US $135

Convenient 2BR Suite in Prime Location with Gym Access & Optional Parking Near McCormick Place and Soldier Field

8.8 (9 Reviews) Apartment

The entire place is yours • 80 m² size • Private parking

Chicago Near South Side • In Grand Boulevard · 4.7km to center

Best Price Match

View Availability

From US $309

The Brown House - A luxurious UChicago Campus stay

10.0 (5 Reviews) Apartment

The entire place is yours • 139 m² size • Free on-site parking

Chicago Woodlawn • In Grand Boulevard · 3.5km to center

Best Price Match

View Availability

From US $576

Beautifully Renovated House 10 mins from Downtown

8.3 (12 Reviews) Holiday_home

The entire place is yours • 297 m² size • Kitchen

Chicago Grand Boulevard • In Grand Boulevard · 500m to center

Best Price Match

View Availability

From US $575

The Black And White Suite

7.1 (20 Reviews) Holiday_home

The entire place is yours • 223 m² size • Free parking

Chicago Grand Boulevard • In Grand Boulevard · 972m to center

Best Price Match

View Availability

From US $210

Chic Euro City Getaway- Close to Downtown

8.4 (29 Reviews) Apartment

The entire place is yours • 111 m² size • Free WiFi

Chicago Grand Boulevard • In Grand Boulevard · 903m to center

Best Price Match

View Availability

From US $206

Stylish Urban Retreat 3 Bedroom Newly Remodeled

8.3 (32 Reviews) Apartment

The entire place is yours • 111 m² size • Free on-site parking

Chicago Grand Boulevard • In Grand Boulevard · 904m to center

Best Price Match

View Availability

From US $189

Cozy Chicago Apartment next to the River

9.5 (15 Reviews) Apartment

The entire place is yours • 93 m² size • Free WiFi

Chicago Bridgeport • In Grand Boulevard · 5.0km to center

Best Price Match

View Availability

From US $348

Hamaline Luxury Guest House

8.5 (7 Reviews) Villa

The entire place is yours • 1400 m² size • Free on-site parking

Chicago Douglas • In Grand Boulevard · 1.6km to center

Best Price Match

View Availability

From US $175

Greater Grand Crossing/Hyde Park

7.4 (23 Reviews) Apartment

The entire place is yours • 12 m² size • Pet friendly

Chicago Greater Grand Crossing • In Grand Boulevard · 4.6km to center

Best Price Match

View Availability

From US $210

Chateau de Woodlawn - Peaceful 3 bedroom apartment.

8.9 (15 Reviews) Apartment

The entire place is yours • 108 m² size • Kitchen

Chicago Woodlawn • In Grand Boulevard · 4.3km to center

Best Price Match

View Availability

From US $170

Bridgeport Place - free parking, McCormick Place-Sox Park

9.1 (17 Reviews) Apartment

The entire place is yours • 60 m² size • Free parking

Chicago Bridgeport • In Grand Boulevard · 4.1km to center

Best Price Match

View Availability

a living room with a couch and a kitchen at Modern 3BR in South Loop with Optional Parking and Gym Access Near McCormick Place, Chinatown and Soldier Field in Chicago

From US $192

Modern 3BR in South Loop with Optional Parking and Gym Access Near McCormick Place, Chinatown and Soldier Field

9.4 (12 Reviews) Apartment

The entire place is yours • 102 m² size • Private parking

Chicago Near South Side • In Grand Boulevard · 4.7km to center

Best Price Match

View Availability

From US $175

Location! Location! 2bd 1bth spacious apartment!

8.3 (13 Reviews) Apartment

The entire place is yours • 48 m² size • Free on-site parking

Chicago Bridgeport • In Grand Boulevard · 4.1km to center

Best Price Match

View Availability

From US $405

Luxe Loft vibe with King Suite - 4BR 3Ba

9.7 (7 Reviews) Apartment

The entire place is yours • 232 m² size • Free on-site parking

Chicago Woodlawn • In Grand Boulevard · 4.8km to center

Best Price Match

View Availability

a living room with a blue couch and a tv at McCormick Place Huge 2BR Cozy Loft Suite with Optional Parking Sleeps 8 Near Soldier Field and Grant Park in Chicago

From US $154

McCormick Place Huge 2BR Cozy Loft Suite with Optional Parking Sleeps 8 Near Soldier Field and Grant Park

9.1 (9 Reviews) Apartment

The entire place is yours • 102 m² size • Private parking

Chicago Near South Side • In Grand Boulevard · 4.7km to center

Best Price Match

View Availability

From US $242

Spacious Bronzeville Apartment

9.8 (5 Reviews) Apartment

The entire place is yours • 139 m² size • Free WiFi

Chicago Douglas • In Grand Boulevard · 1.4km to center

Best Price Match

View Availability

From US $138

Sleek 1-Bedroom Apt in Chicago - East Park Tower 0610 rep

8.8 (6 Reviews) Apartment

The entire place is yours • 58 m² size • Pet friendly

Chicago Hyde Park • In Grand Boulevard · 3.1km to center

Best Price Match

View Availability

From US $275

Modern & Spacious Stay by Northwestern Hospital Bronzeville

9.5 (4 Reviews) Apartment

The entire place is yours • 111 m² size • Free parking

Chicago Grand Boulevard • In Grand Boulevard · 1.1km to center

Best Price Match

View Availability

From US $270

Eco Stay by UChicago, Lakefront & Hyde Park!

9.0 (5 Reviews) Apartment

The entire place is yours • 74 m² size • Free on-site parking

Chicago Woodlawn • In Grand Boulevard · 3.8km to center

Best Price Match

View Availability

From US $159

Cozy & Radiant 2BR Apartment - BStone 605

8.5 (6 Reviews) Apartment

The entire place is yours • 124 m² size • Pet friendly

Chicago Hyde Park • In Grand Boulevard · 2.6km to center

Best Price Match

View Availability

a rooftop patio with furniture and a view of the city at Bright 2BR Apt with Gym and Optional Parking Near Soldier Field, Museum Campus, McCormick Place in Chicago

From US $135

Bright 2BR Apt with Gym and Optional Parking Near Soldier Field, Museum Campus, McCormick Place

8.4 (5 Reviews) Apartment

The entire place is yours • 88 m² size • Private parking

Chicago Near South Side • In Grand Boulevard · 4.6km to center

Best Price Match

View Availability

From US $166

Inviting 2-Bedroom Apt in Hyde Park - The Blackwood rep

7.5 (7 Reviews) Apartment

The entire place is yours • 67 m² size • Pet friendly

Chicago Hyde Park • In Grand Boulevard · 2.6km to center

Best Price Match

View Availability

From US $111

Trendy Studio Apartment in Chicago - Kenwood 103 & 303 rep

8.7 (3 Reviews) Apartment

The entire place is yours • 37 m² size • Pets allowed

Chicago Hyde Park • In Grand Boulevard · 2.9km to center

Best Price Match

View Availability

From US $102

City Charm Studio Apt in Chicago - Kenwood 205

7.6 (5 Reviews) Apartment

The entire place is yours • 37 m² size • Pet friendly

Chicago Hyde Park • In Grand Boulevard · 2.9km to center

Best Price Match

View Availability

From US $133

1BR Stylish & Modern Chicago Apartment - Kenwood 508 rep

7.7 (3 Reviews) Apartment

The entire place is yours • 65 m² size • Pet friendly

Chicago Hyde Park • In Grand Boulevard · 2.5km to center

Best Price Match

View Availability

From US $250

2 BR Apt Near U Chicago Campus & the Lakefront!

7.7 (3 Reviews) Apartment

The entire place is yours • Free on-site parking • Pet friendly

Chicago Kenwood • In Grand Boulevard · 1.8km to center

Best Price Match

View Availability

From US $102

Modern and Minimalist Studio Apartment - Bstone 105 and 108 rep

6.5 (4 Reviews) Apartment

The entire place is yours • 39 m² size • Pet friendly

Chicago Hyde Park • In Grand Boulevard · 3.0km to center

Best Price Match

View Availability

From US $188

Dog-Friendly Apt with Yard 10 Mi to Downtown

7.0 (3 Reviews) Apartment

The entire place is yours • 65 m² size • On-site parking

Chicago Woodlawn • In Grand Boulevard · 4.0km to center

Best Price Match

View Availability

See More Vacation Rentals in Grand Boulevard

About Grand Boulevard Vacation Rentals on NearbyHoliday

Looking for vacation rentals in Grand Boulevard? Compare top options in Chicago.

Find a Vacation Rental and Holiday Home in Grand Boulevard. Compare 38 family vacation homes, private villas, cottages, cabins, and condos in Grand Boulevard.

NearbyHoliday makes it easy to discover vacation rentals in Grand Boulevard that work well for families, groups, and longer stays when you want more room than a standard hotel setup.

Get More Room with NearbyHoliday.

Vacation Rentals: Explore Top Destinations

Explore More

Frequently Asked Questions About Grand Boulevard Vacation Rentals

There are a lot of vacation rentals in Grand Boulevard. If you plan on staying in the Grand Boulevard area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Grand Boulevard: