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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select New Chicago Vacation Homes

A Home Away From Home!
Smart TV, fireplace

A Home Away From Home!

9.6 out of 10, Exceptional, (7)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!
House of TarTar with year long hot tub next to adorable downtown Valparaiso
Terrace/patio

House of TarTar with year long hot tub next to adorable downtown Valparaiso

10.0 out of 10, Exceptional, (75)
"Love the hot tub! "
House of TarTar with year long hot tub next to adorable downtown Valparaiso
Downtown 2 BR Cottage w/ King Bed
Fridge, microwave, oven, stovetop

Downtown 2 BR Cottage w/ King Bed

9.6 out of 10, Exceptional, (5)
"Nicely renovated house, comfortable for adults.Perfect for staying in Valpo during graduation weekend. Many thoughtful touches! Highly recommend for low maintenance travelers!"
The price is CA $214
CA $452 total
includes taxes & fees
Aug 25 - Aug 26
Downtown 2 BR Cottage w/ King Bed
Moody Modern Dunes • Hot tub + Beaches & Trails
Dining

Moody Modern Dunes • Hot tub + Beaches & Trails

10.0 out of 10, Exceptional, (2)
"Jessica has done a truly outstanding job in providing all the little things for making a great stay. The finishes, kitchen & equipment, towels & bedding and snacks/coffee/spices are all best I have seen through many short-term stays. The unit is in a very central location with access to Chesterton, Valpo, the dunes and all transportation. Thanks Jessica!"
The price is CA $218
CA $453 total
includes taxes & fees
Aug 25 - Aug 26
Moody Modern Dunes • Hot tub + Beaches & Trails
Miller Beach Blue Door By The Shore #2
Beach

Miller Beach Blue Door By The Shore #2

7.0 out of 10, Good, (10)
"Perfect!"
Miller Beach Blue Door By The Shore #2
Dunes Homestead - Near Dunes + Lake + Dog Friendly
Fridge, microwave, oven, stovetop

Dunes Homestead - Near Dunes + Lake + Dog Friendly

9.8 out of 10, Exceptional, (21)
"Close to a lot of restaurants and attractions, love the pet friendly atmosphere "
Dunes Homestead - Near Dunes + Lake + Dog Friendly
Valpo Glow & Dunes Flow | Valpo University | Indiana Dunes National Park
Fridge, microwave, oven, stovetop

Valpo Glow & Dunes Flow | Valpo University | Indiana Dunes National Park

10.0 out of 10, Exceptional, (3)
"It was a great place to stay! We would definitely stay here again. "
The price is CA $184
CA $585 total
includes taxes & fees
Sep 2 - Sep 3
Valpo Glow & Dunes Flow | Valpo University | Indiana Dunes National Park
Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
Smart TV, fireplace, foosball

Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake

2.0 star property
10.0 out of 10, Exceptional, (13)
"This was a central location for us to meet with friends, nice accommodations, and a little bit of everything nearby.Hostess was so kind and helpful; house was great and fun for a relaxing weekend from space, to a large fenced backyard to the fire pit. Great place!"
The price is CA $328
CA $736 total
includes taxes & fees
Aug 25 - Aug 26
Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
The Family Retreat, The Family Retreat Oasis
Property grounds

The Family Retreat, The Family Retreat Oasis

2.0 out of 10, (1)
The Family Retreat, The Family Retreat Oasis
Cozy house in Schererville, IN
Exterior detail

Cozy house in Schererville, IN

10.0 out of 10, Exceptional, (15)
"Perfect for the perfect couples getaway"
The price is CA $205
CA $465 total
includes taxes & fees
Sep 7 - Sep 8
Cozy house in Schererville, IN
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
Outdoor dining

Charming 1-bedroom apt in house by creek with AC, in delightful Portage

10.0 out of 10, Exceptional, (5)
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
Spacious 4-bedroom Getaway in Portage, Perfect for family get togethers
Terrace/patio

Spacious 4-bedroom Getaway in Portage, Perfect for family get togethers

8.8 out of 10, Excellent, (3)
"Spacious. Good outdoor area"
Spacious 4-bedroom Getaway in Portage, Perfect for family get togethers
"The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room
Exterior

"The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room

10.0 out of 10, Exceptional, (82)
"We enjoyed our stay at this exceptional property - it was outstanding in every way!"
"The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Terrace/patio

Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

8.8 out of 10, Excellent, (40)
"We had a great stay! The property was perfect- hot tub, plenty of beds, comfortable beds, walking distance to Lake Michigan! Home was comfortable and clean and the managers were easy to reach with questions-just a text away. Would definitely stay here again"
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Mid-Century Cottage Beach Oasis
Terrace/patio

Mid-Century Cottage Beach Oasis

2.0 star property
10.0 out of 10, Exceptional, (5)
"Great stay! Owner has great communication and very responsive. We loved the retro 50's decor and feel. Plenty of room for large families. Nice outdoor patio space. Plenty of parking. The only issue was a small cleaning oversight, but they more than made up for it. Would definitely recommend!"
Mid-Century Cottage Beach Oasis
Relax in style: Chic 2 bedroom haven in brickell.
Fridge, microwave, oven, stovetop

Relax in style: Chic 2 bedroom haven in brickell.

5.4 out of 10, (3)
"This listing is a scam. Someone lives in the property. I was never able to check in. The host never responded. "
Relax in style: Chic 2 bedroom haven in brickell.
Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach
Beach nearby, sun loungers

Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach

10.0 out of 10, Exceptional, (37)
"Amazing stay, and beautiful surroundings "
Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach
Dunes Cottage at Town of Pines Lake Michigan near Indiana Dunes Parks!
Exterior

Dunes Cottage at Town of Pines Lake Michigan near Indiana Dunes Parks!

10.0 out of 10, Exceptional, (13)
"Great place to stay! Quiet street, the home was fully furnished nice yard and firepit. The host would message back in a timely manner. Would definitely stay here again."
The price is CA $218
CA $538 total
includes taxes & fees
Sep 1 - Sep 2
Dunes Cottage at Town of Pines Lake Michigan near Indiana Dunes Parks!
Charming 3-bedroom cottage in Valparaiso with WiFi, AC
Terrace/patio

Charming 3-bedroom cottage in Valparaiso with WiFi, AC

Charming 3-bedroom cottage in Valparaiso with WiFi, AC
Ravine Retreat: Next to Ogden Gardens, Downtown Valparaiso & Close to the Dunes!
Interior

Ravine Retreat: Next to Ogden Gardens, Downtown Valparaiso & Close to the Dunes!

10.0 out of 10, Exceptional, (2)
"Beautiful house in a quiet neighborhood. John has been great to work with over our stay. A great main floor for gathering with 5 bedrooms on the upper floors. The enclosed back patio would be great for small family gatherings. A good size back yard with a nice fire pit. I would highly recommend this space. "
Ravine Retreat: Next to Ogden Gardens, Downtown Valparaiso & Close to the Dunes!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top New Chicago Hotel Reviews

Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

10/10 Excellent
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Miyonna 1-night trip
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Ameristar Casino Hotel East Chicago