| 2 BD Beach Condo | Steps from Lake Michigan | Luxury Vacation Rentals in Chicago | condo | 2 | 4 | $100 |
| Cozy Train Vibes + Rare Parking x3 | Luxury Vacation Rentals in Chicago | apartment | 3 | 6 | $534 |
| Lake Breeze | Cozy Modern Stay | 2 Min To Beach | Luxury Vacation Rentals in Chicago | house | 1 | 3 | $575 |
| The Northside Club House | 2 Living Rooms | Sleeps 8 | Luxury Vacation Rentals in Chicago | house | 4 | 8 | $713 |
| 1820 W Belle Plaine #2 | Luxury Vacation Rentals in Chicago | apartment | 3 | 6 | $745 |
| The Cubs Dugout | 2 Level Retreat | Luxury Vacation Rentals in Chicago | apartment | 4 | 9 | $758 |
| Heron's Nest I Paw Paw Lake Cottages I Erie #2 | Luxury Vacation Rentals in Chicago | cottage | 1 | 5 | — |
| 2 BD Condo I Steps From Lake Michigan | Luxury Vacation Rentals in Chicago | condo | 2 | 4 | — |
| Beach Condo I Steps From Lake Mich | Luxury Vacation Rentals in Chicago | condo | 1 | 4 | — |
| Beach Condo I Steps From Lake Michigan | Luxury Vacation Rentals in Chicago | condo | 1 | 4 | — |
| Bridgeport Boho Chic Vibes | Luxury Vacation Rentals in Chicago | apartment | 2 | 4 | — |
| Cozy 2-Bedroom Apartment | Close to Wrigley | Luxury Vacation Rentals in Chicago | apartment | 2 | 4 | — |
| Gothic-meets-mid-century 2BR in Lakeview | Statement Kitchen + Dining for 4 | Luxury Vacation Rentals in Chicago | apartment | 2 | 4 | — |
| Heron's Nest I Paw Paw Lake Cottages I Huron #1 | Luxury Vacation Rentals in Chicago | cottage | 1 | 4 | — |
| Heron's Nest I Paw Paw Lake Cottages I Michigan #3 | Luxury Vacation Rentals in Chicago | cottage | 1 | 2 | — |
| Heron's Nest I Paw Paw Lake Cottages I Ontario #4 | Luxury Vacation Rentals in Chicago | cottage | 1 | 5 | — |
| Heron's Nest I Paw Paw Lake Cottages I Superior #5 | Luxury Vacation Rentals in Chicago | cottage | 2 | 6 | — |
| Heron's Nest I Paw Paw Lake Cottages I The UP #6 | Luxury Vacation Rentals in Chicago | cottage | 2 | 8 | — |
| Herons Nest I ALL 6 Private Paw Paw Lake Cottages! | Luxury Vacation Rentals in Chicago | cottage | 8 | 28 | — |
| Lake Escape Cottage | Minutes to Paw Paw Lake + Wineries | Luxury Vacation Rentals in Chicago | cottage | 2 | 5 | — |
| Lake Life Retreat| Pool, Hot Tub, Indoor Entertainment | 5 BD Sleeps 14 | Luxury Vacation Rentals in Chicago | house | 5 | 14 | — |
| Little Paw Paw Lake House with Hot Tub | Luxury Vacation Rentals in Chicago | house | 2 | 6 | — |
| Mid-Century Modern 2 BD APT | Walk to Wrigley | Luxury Vacation Rentals in Chicago | apartment | 2 | 4 | — |
| Sunset Skiff, historic lakefront cabin | Luxury Vacation Rentals in Chicago | cabin | 2 | 4 | — |