FEATURED ILLINOIS STAYS
Vacation Rentals in Illinois
Every property is professionally managed with 24/7 guest support and a best-rate guarantee through RedAwning. Tap a card to check availability and book direct.
Showing 47 of 47 properties
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Des Plaines
HOUSE
Modern Home Near Rosemont Allstate Arena O'Hare
3 Bedrooms 2 Bathrooms 6 GuestsDes Plaines, IL, Modern Home Near Rosemont Allstate Arena O'Hare vacation rental.
Hot Tub Pets OK -
Belleville
HOUSE
Spacious Tranquility in Belleville
4 Bedrooms 2.5 Bathrooms 15 GuestsBelleville, IL, Spacious Tranquility in Belleville vacation rental.
Pool Pets OK -
Chicago
HOTEL ROOM
Cabin 301 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 301 at 747 Lofts vacation rental.
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Chicago
HOTEL ROOM
Cabin 104 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 104 at 747 Lofts vacation rental.
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Chicago
HOTEL ROOM
Cabin 206 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 206 at 747 Lofts vacation rental.
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Chicago
HOTEL ROOM
Cabin 208 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 208 at 747 Lofts vacation rental.
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Chicago
HOTEL ROOM
Cabin 201 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 201 at 747 Lofts vacation rental.
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Chicago
HOTEL ROOM
Cabin 103 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 103 at 747 Lofts vacation rental.
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Chicago
HOTEL ROOM
Cabin 105 at 747 Lofts
Studio 1 Bathroom 2 GuestsChicago, IL, Cabin 105 at 747 Lofts vacation rental.
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Evanston
HOUSE
Bright Modern 3Bed 2.5Bath Evanston Home w/Parking
3 Bedrooms 2.5 Bathrooms 9 GuestsEvanston, IL, Bright Modern 3Bed 2.5Bath Evanston Home w/Parking vacation rental.
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Chicago
CONDOMINIUM
Fully Updated Jr. 1 Bed, Steps from Lincoln Park
1 Bedroom 1 Bathroom 4 GuestsChicago, IL, Fully Updated Jr. 1 Bed, Steps from Lincoln Park vacation rental.
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Chicago
APARTMENT
Walk to IL Medical District 1 Bed w/Parking & W/D
1 Bedroom 1 Bathroom 4 GuestsChicago, IL, Walk to IL Medical District 1 Bed w/Parking & W/D vacation rental.
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Chicago
APARTMENT
Cozy 2BR West Town Apt, Ideal for Mid-Term Stays
2 Bedrooms 1 Bathroom 4 GuestsChicago, IL, Cozy 2BR West Town Apt, Ideal for Mid-Term Stays vacation rental.
Pets OK -
Chicago
HOTEL ROOM
Cabin 307 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 307 at 747 Lofts vacation rental.
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Ottawa
HOUSE
Secluded Woodland Retreat Near Starved Rock Park
4 Bedrooms 3.5 Bathrooms 10 GuestsOttawa, IL, Secluded Woodland Retreat Near Starved Rock Park vacation rental.
Pets OK -
Rolling Meadows
HOUSE
Comforting Retreat Near Woodfield Mall
2 Bedrooms 1 Bathroom 6 GuestsRolling Meadows, IL, Comforting Retreat Near Woodfield Mall vacation rental.
Pets OK -
Des Plaines
RESIDENCE
Contemporary Retreat in the Heart of Des Plaines
3 Bedrooms 1.5 Bathrooms 10 GuestsDes Plaines, IL, Contemporary Retreat in the Heart of Des Plaines vacation rental.
Pets OK -
Belleville
RESIDENCE
Belleville Beauty- Luxury Stay for Work or Stay for Play…
4 Bedrooms 2 Bathrooms 7 GuestsBelleville, IL, Belleville Beauty- Luxury Stay for Work or Stay for Play either way this is the perfect property for you! vacation rental.
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Chicago
HOTEL ROOM
Cabin 106 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 106 at 747 Lofts vacation rental.
Pets OK -
Chicago
HOTEL ROOM
Cabin 203 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 203 at 747 Lofts vacation rental.
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Chicago
HOTEL ROOM
Cabin 304 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 304 at 747 Lofts vacation rental.
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Chicago
APARTMENT
Spacious 2 Bed/2 Bath Apartment in West Town!
2 Bedrooms 2 Bathrooms 4 GuestsChicago, IL, Spacious 2 Bed/2 Bath Apartment in West Town! vacation rental.
Pets OK -
Chicago
HOTEL ROOM
Cabin 207 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 207 at 747 Lofts vacation rental.
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Chicago
CONDOMINIUM
Heart of East Village 2-Bed 2-Bath Peaceful Oasis
2 Bedrooms 2 Bathrooms 4 GuestsChicago, IL, Heart of East Village 2-Bed 2-Bath Peaceful Oasis vacation rental.
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Chicago
TOWNHOUSE
Charming Andersonville Coach House 3BR 2,5BA
3 Bedrooms 2.5 Bathrooms 5 GuestsChicago, IL, Charming Andersonville Coach House 3BR 2,5BA vacation rental.
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Chicago
HOTEL ROOM
Cabin 205 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 205 at 747 Lofts vacation rental.
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Chicago
HOTEL ROOM
Cabin 102 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 102 at 747 Lofts vacation rental.
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Chicago
APARTMENT
Great 1 BR Apartment in West Town
1 Bedroom 1 Bathroom 3 GuestsChicago, IL, Great 1 BR Apartment in West Town vacation rental.
Pets OK -
Chicago
APARTMENT
Bright 2 Bed w/Office on Historic Logan Boulevard
2 Bedrooms 1 Bathroom 6 GuestsChicago, IL, Bright 2 Bed w/Office on Historic Logan Boulevard vacation rental.
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Glenview
HOUSE
Charming Contemporary Family Home
3 Bedrooms 1 Bathroom 6 GuestsGlenview, IL, Charming Contemporary Family Home vacation rental.
Pets OK -
Des Plaines
HOUSE
Spacious Retreat Near Convention Centers
4 Bedrooms 1 Bathroom 10 GuestsDes Plaines, IL, Spacious Retreat Near Convention Centers vacation rental.
Pets OK -
Chicago
HOTEL ROOM
Cabin 204 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 204 at 747 Lofts vacation rental.
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Chicago
HOTEL ROOM
Cabin 308 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 308 at 747 Lofts vacation rental.
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Chicago
HOTEL ROOM
Cabin 305 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 305 at 747 Lofts vacation rental.
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Chicago
HOTEL ROOM
Cabin 306 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 306 at 747 Lofts vacation rental.
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Chicago
HOTEL ROOM
Cabin 302 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 302 at 747 Lofts vacation rental.
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Chicago
HOTEL ROOM
Cabin 101 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 101 at 747 Lofts vacation rental.
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Chicago
HOTEL ROOM
Cabin 303 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 303 at 747 Lofts vacation rental.
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Chicago
CONDOMINIUM
Elegant Condo-Walk to Wrigley Field, 32+ Nights
3 Bedrooms 2.5 Bathrooms 4 GuestsChicago, IL, Elegant Condo-Walk to Wrigley Field, 32+ Nights vacation rental.
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Chicago
CONDOMINIUM
2bd River North Million Dollar Views! Parking Incl
2 Bedrooms 2 Bathrooms 6 GuestsChicago, IL, 2bd River North Million Dollar Views! Parking Incl vacation rental.
Pool -
Chicago
CONDOMINIUM
Heart of Wrigleyville 4bd 2ba Long Stay Modern Apt
4 Bedrooms 2 Bathrooms 10 GuestsChicago, IL, Heart of Wrigleyville 4bd 2ba Long Stay Modern Apt vacation rental.
Pets OK -
Chicago
CONDOMINIUM
2bd River North Million Dollar Views! Parking Incl
2 Bedrooms 1 Bathroom 4 GuestsChicago, IL, 2bd River North Million Dollar Views! Parking Incl vacation rental.
Pool -
Chicago
CONDOMINIUM
Newly Renovated 3BR/2BA in Heart of Andersonville
3 Bedrooms 2 Bathrooms 6 GuestsChicago, IL, Newly Renovated 3BR/2BA in Heart of Andersonville vacation rental.
Pets OK -
Oglesby
HOUSE
Oglesby Vacation Home
6 Bedrooms 4.5 Bathrooms 13 GuestsOglesby, IL, Oglesby Vacation Home vacation rental.
Pool Pets OK -
Chicago
APARTMENT
2 Bedroom Apartment in West Town
2 Bedrooms 1 Bathroom 4 GuestsChicago, IL, 2 Bedroom Apartment in West Town vacation rental.
Pets OK -
Chicago
APARTMENT
Long Term Rental: 3BR/2BA River West Condo
3 Bedrooms 2 Bathrooms 7 GuestsChicago, IL, Long Term Rental: 3BR/2BA River West Condo vacation rental.
Pets OK -
Chicago
HOTEL ROOM
Cabin 202 at 747 Lofts
Multiple UnitsChicago, IL, Cabin 202 at 747 Lofts vacation rental.