Holiday rentals near State Street
We found 3,046 holiday rentals — enter your dates for availability
Choose the right holiday home within easy reach of State Street. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as Wi-Fi and parking. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - State Street
Showing deals for:8 Aug - 15 Aug
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago
9.89.8 out of 10 rating
Exceptional
(14 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
7% off
Price is NZ$12,472
NZ$12,472
NZ$1,782 per night
includes taxes & fees
Image gallery for City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
1010 out of 10 rating
Exceptional
(27 reviews)
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
Chicago, IL
11% off
Price is NZ$12,466
NZ$12,466
NZ$1,781 per night
includes taxes & fees
Image gallery for #1613 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(16 reviews)
#1613 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,069
NZ$4,069
NZ$581 per night
includes taxes & fees
Image gallery for #1514 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(10 reviews)
#1514 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,344
NZ$3,344
NZ$478 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.69.6 out of 10 rating
Exceptional
(8 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$9,459
NZ$9,459
NZ$1,351 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Game Room Access | Chicago
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Kasa | Family Friendly 3 BD + Game Room Access | Chicago
Chicago, Illinois
8% off
Price is NZ$10,400
NZ$10,400
NZ$1,486 per night
includes taxes & fees
Image gallery for Spacious,Chic & Steps from MichiganAve|The Hermes
1010 out of 10 rating
Exceptional
(7 reviews)
Spacious,Chic & Steps from MichiganAve|The Hermes
Chicago, Illinois
8% off
Price is NZ$9,228
NZ$9,228
NZ$1,318 per night
includes taxes & fees
Image gallery for Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
9.89.8 out of 10 rating
Exceptional
(32 reviews)
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,285
NZ$6,285
NZ$898 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$8,467
NZ$8,467
NZ$1,210 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(13 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
7% off
Price is NZ$13,642
NZ$13,642
NZ$1,949 per night
includes taxes & fees
Image gallery for 2BR Designer Loft: Modern Luxe in City Center
1010 out of 10 rating
Exceptional
(5 reviews)
2BR Designer Loft: Modern Luxe in City Center
Chicago, Illinois
8% off
Price is NZ$7,166
NZ$7,166
NZ$1,024 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago
Chicago, Illinois
8% off
Price is NZ$10,400
NZ$10,400
NZ$1,486 per night
includes taxes & fees
Image gallery for Downtown Chicago Studio in Prime Location
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Downtown Chicago Studio in Prime Location
Chicago, Illinois
5% off
Price is NZ$4,616
NZ$4,616
NZ$659 per night
includes taxes & fees
Image gallery for Kasa | Inviting 1 BD + Game Room Access | Chicago
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Kasa | Inviting 1 BD + Game Room Access | Chicago
Chicago, Illinois
8% off
Price is NZ$5,232
NZ$5,232
NZ$747 per night
includes taxes & fees
Image gallery for #2012 - Kasa Magnificent Mile Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
#2012 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,069
NZ$4,069
NZ$581 per night
includes taxes & fees
Image gallery for Kasa | Relaxing 1 BD + Near Local Eateries | Chicago
1010 out of 10 rating
Exceptional
(12 reviews)
Kasa | Relaxing 1 BD + Near Local Eateries | Chicago
Chicago, Illinois
8% off
Price is NZ$3,871
NZ$3,871
NZ$553 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Pet Friendly | Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Kasa | Family Friendly 3 BD + Pet Friendly | Chicago
Chicago, Illinois
8% off
Price is NZ$10,400
NZ$10,400
NZ$1,486 per night
includes taxes & fees
Image gallery for 2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
8.08.0 out of 10 rating
Very good
(13 reviews)
2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
Chicago, IL
11% off
Price is NZ$9,869
NZ$9,869
NZ$1,410 per night
includes taxes & fees
Image gallery for #2011 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(8 reviews)
#2011 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,344
NZ$3,344
NZ$478 per night
includes taxes & fees
Image gallery for #1511 - Kasa Magnificent Mile Chicago
9.69.6 out of 10 rating
Exceptional
(15 reviews)
#1511 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,344
NZ$3,344
NZ$478 per night
includes taxes & fees
Image gallery for Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views
9.49.4 out of 10 rating
Exceptional
(39 reviews)
Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,566
NZ$6,566
NZ$938 per night
includes taxes & fees
Image gallery for Chic Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(45 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
7% off
Price is NZ$6,130
NZ$6,130
NZ$876 per night
includes taxes & fees
Image gallery for Stylish Corner 2BR in the Loop | City & Lake Views
9.69.6 out of 10 rating
Exceptional
(50 reviews)
Stylish Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
7% off
Price is NZ$6,179
NZ$6,179
NZ$883 per night
includes taxes & fees
Image gallery for #1515 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(23 reviews)
#1515 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,069
NZ$4,069
NZ$581 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - State Street
Spacious two bedroom condo with a cozy feel!
Sleeps 4 · 2 bedrooms · 2 bathrooms
8.08.0 out of 10
Very goodvery good
4 reviews(4 reviews)
Lovely 2 Bed. 3 Miles from DT w/ Free Parking
Sleeps 6 · 2 bedrooms · 1 bathroom
8.08.0 out of 10
Very goodvery good
34 reviews(34 reviews)
Woodlawn Oasis...10 Minutes to Dining & Downtown
Sleeps 12 · 3 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Elegant Escape 4BR/3BA near UChicago & Obama Home
Sleeps 12 · 4 bedrooms · 3 bathrooms
Berwyn Bungalow - Explore Chicago from a Modern, Hip Bungalow vacation home.
Sleeps 10 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Spacious 5-bedroom house with movie room, game room and more!
Sleeps 16 · 5 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value