StayThereDirect vacation rentals in Chicago, IL
Explore 50 stays from 8 independent hosts across 2 booking platforms. Select dates to check live availability and the host's current total.
DIRECT INVENTORY
Stays to explore in Chicago
Availability and final prices depend on your dates. These pages link to each property's direct booking source.
Direct stay · Sleeps 6Modern Corner 2BR in Streeterville | Roof Deck | Lake Viewsstaywell-hospitality.guestybookings.com
Direct stay · Sleeps 6Stunning Corner 2BR in the Loop | City & Lake Viewsstaywell-hospitality.guestybookings.com
Direct stay · Sleeps 6Stylish Corner 2 Bedroom in the Heart of Chicago | Roof Deckstaywell-hospitality.guestybookings.com
Direct stay · Sleeps 8Two-Story Penthouse, City Views, Pool, Gymthepenthouseatgrandplaza.guestybookings.com
Direct stay · Sleeps 250th Floor Mag Mile Views, Balcony, Pool, Gymthepenthouseatgrandplaza.guestybookings.com
Direct stay · Sleeps 451st Floor MagMile Penthouse Views Balcony Poolthepenthouseatgrandplaza.guestybookings.com
Direct stay · Sleeps 452nd Floor MagMile Penthouse Views Fireplace Poolthepenthouseatgrandplaza.guestybookings.com
Direct stay · Sleeps 452nd Floor Penthouse with Skyline Views and Poolthepenthouseatgrandplaza.guestybookings.com
Direct stay · Sleeps 855th Floor Penthouse with Award-Winning Viewsthepenthouseatgrandplaza.guestybookings.com
Direct stay · Sleeps 82-Story Penthouse Views, Fireplace, Pool, Gymthepenthouseatgrandplaza.guestybookings.com
Direct stay · Sleeps 4Boulevard Stays River North Retreat Near Magnificent Mileboulevardstays.guestybookings.com
Direct stay · Sleeps 5Steps from Midway Airport, 2BR 1BA Garden Unitdreamchicagorentals.guestybookings.comHow StayThere helps
StayThere is a discovery service, not the property manager or merchant. Search results combine direct-booking inventory from professional vacation-rental websites. When dates are selected, StayThere requests current availability and pricing from the booking provider, then sends you to the host to complete the reservation.
Always confirm the final price, cancellation terms, house rules, and property details on the host's checkout page.