Chicago, Illinois Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Chicago, Illinois on RentalSaver.com!

Chicago Rentals

From $245 per night (USD)
VRBO
Charming 1BR in Old Irving
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Nestled in one of Chicago’s most beloved neighborhoods, this cozy and stylish one-bedroom apartment offers the ...
From $245 per night (USD)
VRBO
From $211 per night (USD)
Expedia
Cozy 1-Bedroom Apartment - Sunnyside 2N
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Enjoy a stylish experience at this centrally-located place. The Space: This fully furnished 1-bedroom apartmen ...
From $211 per night (USD)
Expedia
From $391 per night (USD)
VRBO
Stylish 4BR South Loop Home State 23-202
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Experience Chicago in style at our beautifully furnished four-bedroom house, complete with three full bathrooms ...
From $391 per night (USD)
VRBO
From $440 per night (USD)
Expedia
Cozy 3BR Gem in North Center
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: This spacious and stylish 3-bedroom gem is perfect for families, groups, or business travelers seeking comfort ...
From $440 per night (USD)
Expedia
From $178 per night (USD)
VRBO
Ideal & Spacious 1BR Apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Make lasting memories with the family in this chic and comfy space. The Space: The bedrooms feature comfortabl ...
From $178 per night (USD)
VRBO
From $299 per night (USD)
Expedia
Your 2BR Home in the City
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to Your 2BR Home in the City – where comfort, convenience, and style come together. This thoughtfully d ...
From $299 per night (USD)
Expedia
From $202 per night (USD)
VRBO
2BR Cozy & Functional Unit
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: A 2-bedroom, 1-bath apartment offering a comfortable, well-designed space—perfect for a relaxed and convenient ...
From $202 per night (USD)
VRBO
From $182 per night (USD)
Expedia
Chic 2BR Haven Near Irving Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Discover your Chicago home-away-from-home in the heart of Old Irving Park! This 2BR gem sits on a quiet, leafy ...
From $182 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Simple, Comfy Living - Furnished 1BR Pad
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Keep it simple at this peaceful and centrally-located place. The spacious living area is filled with natural l ...
From $220 per night (USD)
VRBO
From $353 per night (USD)
Expedia
3BR | Complete & Well-Located
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Our 3-bedroom apartment is warm, welcoming, and set up with all the comforts of home — including a full kitchen ...
From $353 per night (USD)
Expedia
From $258 per night (USD)
VRBO
Bright & Airy 1-Bedroom Unit
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Furnished 1-bedroom apartment with 1 bathroom, a fully equipped kitchen, and dining area. Designed to sleep up ...
From $258 per night (USD)
VRBO
From $375 per night (USD)
Expedia
Hyde Park Haven | 2BR Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Your cozy 2BR retreat in the heart of Chicago’s historic Hyde Park neighborhood. What You’ll Love: • 2 Comfort ...
From $375 per night (USD)
Expedia
From $188 per night (USD)
VRBO
Bright & Modern 1BR in Hyde Park
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Enjoy a comfortable stay in our bright and modern one-bedroom apartment in the vibrant Hyde Park neighborhood. ...
From $188 per night (USD)
VRBO
From $448 per night (USD)
Expedia
Sleek Style 3BR Haven - Free Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: A modern home that’s both stylish and practical, offering comfort and everyday ease. Spacious 3-Bedroom Layout ...
From $448 per night (USD)
Expedia
From $186 per night (USD)
VRBO
Delightful 1BR Apt in Ravenswood
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Discover a one-of-a-kind escape in this uniquely styled 1-bedroom apartment. With modern design, cozy furnishin ...
From $186 per night (USD)
VRBO
From $187 per night (USD)
Expedia
Cozy & Modern Getaway 1BR Apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: A chic spot to kick back, relax, and enjoy some fun together. The Space: This charming home has plenty of spac ...
From $187 per night (USD)
Expedia
From $395 per night (USD)
VRBO
Upscale 4BR Retreat: Wicker Park
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Welcome to your spacious 4-bedroom getaway in the heart of Wicker Park—Chicago’s most vibrant and eclectic neig ...
From $395 per night (USD)
VRBO
From $202 per night (USD)
Expedia
Modern 1BR in Historic HydePark
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to your cozy home-away-from-home in the vibrant Hyde Park neighborhood of Chicago! This charming 1-bedr ...
From $202 per night (USD)
Expedia
From $224 per night (USD)
VRBO
Your Perfect 2BR Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Escape to this cozy 2BR vacation home, the perfect retreat for families or small groups! Located in a peaceful ...
From $224 per night (USD)
VRBO
From $452 per night (USD)
Expedia
Spacious 4BR Near Wicker Park
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Welcome to this spacious and inviting 2-level apartment—perfect for families or groups! This bright and spaciou ...
From $452 per night (USD)
Expedia
From $215 per night (USD)
VRBO
Sleek & Functional 2-Bedroom Apt
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Perfect for small families or friends, this cozy 2BR/1BA unit has two comfy queen beds, a full kitchen, fast Wi ...
From $215 per night (USD)
VRBO
From $207 per night (USD)
Expedia
Paradise 1BR Apt in Lincoln Park
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Experience the perfect blend of comfort and style in this thoughtfully designed space, created to offer you a r ...
From $207 per night (USD)
Expedia
From $403 per night (USD)
VRBO
Furnished 3BR Apt w/ Laundry
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: We've set up our 3-bedroom apartment to be as comfy and welcoming as possible—like a little home away from home ...
From $403 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Explore Hyde Park: 2BR Apt on Blackstone Ave
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Make our 2-bedroom, 1-bathroom apartment on S Blackstone Ave your home base for exploring the historic Hyde Par ...
From $220 per night (USD)
Expedia
From $156 per night (USD)
VRBO
Cute 1BR in Heart of Lincoln Sq
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Cute apartment near Lincoln Square shops and restaurants. Lively area near public transportation. Near the lake ...
From $156 per night (USD)
VRBO
From $199 per night (USD)
Expedia
Deluxe 1BR Near Shops & Cafés
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Enjoy the perfect blend of comfort and location in this stylish 1-bedroom apartment. Featuring a cozy living sp ...
From $199 per night (USD)
Expedia
From $182 per night (USD)
VRBO
1BR Modern Apt in Lakeview
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: A chic spot to kick back, relax, and enjoy some fun together. The Space: This home has everything you need to ...
From $182 per night (USD)
VRBO
From $228 per night (USD)
Expedia
Stylish 1BR Apt in Lakeview
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Kick back and relax in this calm, stylish space. Featuring a modern design, the apartment boasts a spacious liv ...
From $228 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Contemporary 2BR Apartment in Vibrant Hyde Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Nestled on historic E Hyde Park Blvd, this 2-bedroom apartment offers a fantastic opportunity to embrace the Hy ...
From $295 per night (USD)
VRBO
From $236 per night (USD)
Expedia
Comfortable 2BR Chicago Apt
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Warm, comfy, and perfect for families—this 2BR/1BA in East Albany Park features two spacious king beds, a full ...
From $236 per night (USD)
Expedia
From $187 per night (USD)
VRBO
Vibrant 1BR Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The perfect blend of comfort and style for a fun, relaxing stay. The Space: This charming home has plenty of s ...
From $187 per night (USD)
VRBO
From $226 per night (USD)
Expedia
Hyde Park 1BR w/ Charm
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Your perfect home away from home in the heart of Chicago's historic Hyde Park neighborhood. The Space: The Spa ...
From $226 per night (USD)
Expedia
From $219 per night (USD)
VRBO
Chic Retreat: Cozy 1BR Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Sink into comfort in this stylish hideaway. Modern 1BR/1BA in the heart of Hyde Park—perfect for couples, solo ...
From $219 per night (USD)
VRBO
From $232 per night (USD)
Expedia
Cozy 3BR with Contemporary Vibe
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: This cozy 3-bedroom apartment offers a perfect blend of comfort and modern style. With spacious rooms and an op ...
From $232 per night (USD)
Expedia
From $210 per night (USD)
VRBO
1BR Modern Apartment near City Center
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: This unique place boasts a distinctive style all its own, blending carefully curated design elements with a war ...
From $210 per night (USD)
VRBO
From $239 per night (USD)
Expedia
Cozy 2BR Apt near Parks & Shops
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Enjoy the best of city living in this centrally located 2BR apartment—just steps from parks, shops, and local d ...
From $239 per night (USD)
Expedia
From $212 per night (USD)
VRBO
1BR in Prime Hyde Park Apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Enjoy a stylish experience at this centrally-located place. The Space: Experience the best of urban living in ...
From $212 per night (USD)
VRBO
From $172 per night (USD)
Expedia
1BR Airy Apartment w/ Wi-Fi
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to your cozy Cragin hideaway! This fun and comfy 1BR/1BA is perfect for couples or solo travelers. Snug ...
From $172 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Spacious 4BR Retreat
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Welcome to your home away from home in the charming Rogers Park neighborhood! This spacious 4-bedroom, 2-bath a ...
From $416 per night (USD)
VRBO
From $182 per night (USD)
Expedia
1BR Serene and Cozy Chicago Apt!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Discover comfort in this serene 1BR Chicago apartment, perfect for solo travelers or couples. Nestled in a quie ...
From $182 per night (USD)
Expedia
From $676 per night (USD)
VRBO
Spacious 5-bedroom house great for large groups
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Light and airy custom built home across from Humboldt Park with expansive views of the Humboldt Park pond/lake. Spacious ...
From $676 per night (USD)
VRBO
From $240 per night (USD)
Expedia
1BR Chic & Sunny Place
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Feel at home in our furnished 1-bedroom with a comfy living room, full kitchen, and private bath. Everything yo ...
From $240 per night (USD)
Expedia
From $248 per night (USD)
VRBO
Twice as Nice: Chic 2BR Stay with Style & Space
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to your home away from home! This cozy 2BR retreat is all about comfort with a side of style. Located n ...
From $248 per night (USD)
VRBO
From $269 per night (USD)
Expedia
Sleek 1BR Apt w/ Laundry
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Comfortable and fully furnished 1BR apartment with all the essentials for a smooth, easy stay. The Space: Our ...
From $269 per night (USD)
Expedia
From $180 per night (USD)
VRBO
Prime City Stay in a 1BR Apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Fully furnished 1-bedroom apartment in a prime location. Move-in ready with everything you need for comfortable ...
From $180 per night (USD)
VRBO
From $252 per night (USD)
Expedia
The One: A 1BR Stay That Feels Like Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: This is more than just a place to stay; it’s your cozy, personal retreat. With soft lighting, comfy furnishings ...
From $252 per night (USD)
Expedia
From $243 per night (USD)
VRBO
3BR Apt - Prime & Spacious
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: A 3-bedroom place with 2 bathrooms, full kitchen, in-unit washer/dryer, and Wi-Fi. There's a dining table too, ...
From $243 per night (USD)
VRBO
From $189 per night (USD)
Expedia
Great Layout – Spacious 2BR Apt
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Your perfect 2-bedroom retreat — spacious layout, modern furnishings, and instant comfort. The Space: This is ...
From $189 per night (USD)
Expedia
From $298 per night (USD)
VRBO
Perfect Stay - Modern 2BR Unit
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Summary: Welcome to your happy place in Lakeview! This fun and inviting 2BR/1BA is perfect for a small group or family. ...
From $298 per night (USD)
VRBO
From $284 per night (USD)
Expedia
2BR Steps from Wrigley Field
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to your home base in the heart of Chicago’s vibrant Lakeview/Wrigleyville neighborhood! This roomy and ...
From $284 per night (USD)
Expedia
From $180 per night (USD)
VRBO
1BR Gem by Shops & Dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: 1BR Gem by Shops & Dining – Discover comfort and convenience in this stylish 1-bedroom apartment, perfectly loc ...
From $180 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Stylish 1BR in Lakeview Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Step into comfort and style in this beautifully designed 1-bedroom apartment nestled in vibrant Lakeview. With ...
From $204 per night (USD)
Expedia
From $129 per night (USD)
VRBO
Walk to Metra: Long-Term Getaway in Chicago!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Near Public Transportation | Traveling Nurses Welcome | In-Unit Laundry Your next extended stay in Chicago starts here! ...
From $129 per night (USD)
VRBO
From $218 per night (USD)
Expedia
1BR Well-Equipped Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: All the comforts of home in a stylish, fully furnished 1BR—ideal for short or long stays. The Space: Our fully ...
From $218 per night (USD)
Expedia
From $202 per night (USD)
VRBO
Well-Appointed &Vibrant 2BR Apt
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Bring the whole crew to this trendy spot – perfect for family fun! The Space: The bedrooms feature comfortable ...
From $202 per night (USD)
VRBO
From $252 per night (USD)
Expedia
A chic second-floor plant-filled retreat in Chicago's Logan Square neighborhood.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Experience the charm of this Logan Square Greystone apartment, a chic second-floor plant-filled retreat in Chicago's vib ...
From $252 per night (USD)
Expedia
From $3219 per night (USD)
VRBO
Exclusive Group Getaway in Vibrant West Loop
Bedrooms:
8
Bathrooms:
9
Sleeps:
22
Summary: 'The Cubist' is the ultimate destination for your group's special occasion, offering four luxurious apartments ...
From $3219 per night (USD)
VRBO
From $254 per night (USD)
Expedia
Complete 1BR Home Sum
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Step into comfort and style in this beautifully furnished 1-bedroom apartment designed for easy living. With sl ...
From $254 per night (USD)
Expedia
From $227 per night (USD)
VRBO
Bright 1BR Unit in a Prime Spot
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Experience the ease of living in a bright, fully furnished 1-bedroom apartment in a desirable neighborhood. Th ...
From $227 per night (USD)
VRBO
From $196 per night (USD)
VRBO
In Chicago, Near Beverly & Evergreen Park Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This stylish unit... - Conveniently located 20 mins from Downtown Chicago. - 9 mins from Walmart, Target, Ross, Burling ...
From $196 per night (USD)
VRBO
From $240 per night (USD)
VRBO
Brand New 2BR Chicago City Escape
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to your chic, new retreat in Chicago! This brand new luxury apartment is meticulously designed for comf ...
From $240 per night (USD)
VRBO
From $210 per night (USD)
Expedia
Perfect 1BR Spot near Attractions
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Enjoy a fully furnished 1BR/1BA unit with a full kitchen and cozy living space. Conveniently located near parks ...
From $210 per night (USD)
Expedia
From $154 per night (USD)
VRBO
Sunlit Studio with City Charm
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Bask in natural light at Sunlit Studio with City Charm a thoughtfully designed space tucked in the heart of the ...
From $154 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Urban Studio Hideaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Nestled in Chicago’s lively Lakeview neighborhood, this area blends classic charm with modern city living. Stro ...
From $215 per night (USD)
Expedia
From $189 per night (USD)
VRBO
Cozy Charm Studio Apt in Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Step into this uniquely styled studio that blends comfort, function, and personality in one cozy space. Perfect ...
From $189 per night (USD)
VRBO
From $239 per night (USD)
Expedia
Cozy 1BR Apt Near Dining & Shops
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Enjoy a stylish stay in this centrally located 1-bedroom retreat, thoughtfully designed for comfort and conveni ...
From $239 per night (USD)
Expedia
From $252 per night (USD)
VRBO
NEW Eco Stay by UChicago, Lakefront & Hyde Park!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Enjoy comfort and sustainability in this beautifully designed South Side retreat. Located in a modern, solar-powered gre ...
From $252 per night (USD)
VRBO
From $306 per night (USD)
Expedia
3 Bed 2.5 Bath Chicago Retreat w Balcony & Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Welcome to our charming 3-bedroom, 2.5-bathroom home in the vibrant Pilsen neighborhood of Chicago! Perfect for ...
From $306 per night (USD)
Expedia
From $452 per night (USD)
VRBO
Brand-New West Loop 3BR + City Views for Families
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: Experience brand-new luxury at 'The Lyric,' a stunning 3BR in in West Loop’s vibrant Fulton District. You're ...
From $452 per night (USD)
VRBO
From $84 per night (USD)
Expedia
Blueground | Rush & Division, fitness center, nr Lincoln Park
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this lovely one bedroom Blueground apartment. You’ll love coming h ...
From $84 per night (USD)
Expedia
From $329 per night (USD)
VRBO
Updated, Prime Location, Parking Avail. - LP
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Bask in natural light and timeless style in this beautifully updated 1BR, set on one of Lincoln Park’s most coveted, man ...
From $329 per night (USD)
VRBO
From $416 per night (USD)
Expedia
The Prestige: Designer 3BR/2BA in Prime Location
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to The Prestige- where luxury meets comfort. This spacious 3-bed, 2-bath condo sleeps 8 (3 king beds & 1 pull-ou ...
From $416 per night (USD)
Expedia
From $536 per night (USD)
VRBO
2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $536 per night (USD)
VRBO
From $254 per night (USD)
Expedia
Cozy Room with Rooftop Lounge & City Views in River North
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 355 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $254 per night (USD)
Expedia
From $606 per night (USD)
VRBO
2 Luxury Queen with Rooftop Lounge & City Views Near Attractions
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $606 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Luxury Unit with Rooftop Lounge & Spectacular City Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 248 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $220 per night (USD)
Expedia
From $303 per night (USD)
VRBO
Modern Suite with Rooftop Lounge & Views of Downtown Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 301 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $303 per night (USD)
VRBO
From $512 per night (USD)
Expedia
2 Relaxing Rooms with Rooftop Lounge & City Views of Chicago
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $512 per night (USD)
Expedia
From $652 per night (USD)
VRBO
2 Spacious King Room with Rooftop Lounge & Scenic Views of Chicago
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $652 per night (USD)
VRBO
From $265 per night (USD)
Expedia
Spacious Room with Rooftop Lounge & Scenic Views of Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 355 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $265 per night (USD)
Expedia
From $153 per night (USD)
VRBO
15mins DT | Wicker Park Gem | Sleeps 7 | FreePark
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Stylish 2BR/1BA unit in trendy Humboldt/Wicker Park. Unwind in a cozy, modern space with vibrant decor, a fully equipped ...
From $153 per night (USD)
VRBO
From $295 per night (USD)
Expedia
Come experience The Lake Shore!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Come experience the Lake Shore! A corporate apartment that boast comfort, class and the PERFECT location to explore any ...
From $295 per night (USD)
Expedia
From $277 per night (USD)
VRBO
Bright + Cozy 3-bedroom apartment, Sleeps 8 plus Crib, Prime HP/Wicker Park
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
3B1B unit for 8 people plus a crib. Great West Wicker Park, Humboldt Park location (in coveted 60622 area code) just 0.9 ...
From $277 per night (USD)
VRBO
From $226 per night (USD)
Expedia
Charming Cozy 2BR Haven w/Crib Near Hip WickerPark
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
2B1B unit for 6 people plus a crib. Great West Wicker Park location (in coveted 60622 area code) just 0.9 miles from Dam ...
From $226 per night (USD)
Expedia
From $343 per night (USD)
VRBO
Sunny & Spacious Bucktown 3Bd/2Ba w/Laundry
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful Condo Quality Fully Furnished and Renovated space for monthly rental. A super spacious 3 bedroom, 2 bath apa ...
From $343 per night (USD)
VRBO
From $322 per night (USD)
Expedia
Flexhome East Village 2BR H2
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The space: The apartment sleeps up to 4 with a comfy queen bed in each room plus flexible seating areas so you can work ...
From $322 per night (USD)
Expedia
From $218 per night (USD)
VRBO
Flexhome Ukrainian Village 2BR D1
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Please review the House Rules before booking as we reserve the right to end the stay if violated: 1. No parties, gather ...
From $218 per night (USD)
VRBO
From $781 per night (USD)
Expedia
Devon House Summary:
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: One of the 77 Chicago Communities, Norwood Park is just 15 miles from Downtown Chicago & less than 15 minutes f ...
From $781 per night (USD)
Expedia
From $251 per night (USD)
VRBO
2BR Brownstone 7-minutes to Event Centers, Downtown, & Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to The Garden Oasis — your cozy home base in a historic Chicago Brownstone! Live like a local just minutes from ...
From $251 per night (USD)
VRBO
From $340 per night (USD)
Expedia
Bright 3BR Retreat Near McCormick + Museum Campus
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to The State Suite — a modern, artfully designed 3-bedroom, 1-bath apartment perfect for everyone! Just minutes ...
From $340 per night (USD)
Expedia
From $282 per night (USD)
VRBO
Lovely Garden Set up is Perfect for Your Morning Coffee or a Drink After Some Great Blues Music at Kingston Mines by AllSet Turnover
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This perfectly located 2 BD/2 BA unit is waiting for you to call it home for your trip to gorgeous Lincoln Park! Make y ...
From $282 per night (USD)
VRBO
From $719 per night (USD)
Expedia
Spectacular Gold Coast Villa Near Beach w/ Parking
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to the Gold Coast Villa Retreat — a stunning, fully renovated private home designed for families, groups, and bu ...
From $719 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Spacious 2BR - 10 mins from Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your home away from home in Chicago’s Near West Side neighborhood—just 10 minutes from downtown! This spaci ...
From $222 per night (USD)
VRBO
From $174 per night (USD)
Expedia
Lower level luxury
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Discover Chicago like a true local in this stylish 2-bedroom lower-level retreat. Perfect for small groups, this tranqui ...
From $174 per night (USD)
Expedia
From $256 per night (USD)
VRBO
1 GB Wi-Fi | Reserved Parking | Sleeps 4
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: The pictures are from another apartment we have in this building. The design, furniture and layout of the apart ...
From $256 per night (USD)
VRBO
From $182 per night (USD)
Expedia
Cozy Condo, Sleeps 2!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Stay in the heart of Old Town, Chicago at this stylish 1-bedroom, 1-bathroom condo with a king bed, in-unit lau ...
From $182 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Stylish Sleeps 6 1 Free Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Stay in this modern 2BR, 1BA apartment in Lakeview, Chicago, perfect for families, friends, or groups of up to ...
From $368 per night (USD)
VRBO
From $853 per night (USD)
VRBO
Entire Home in Historic Logan Square with private backyard, parking available.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Kick back & relax in this calm & stylish space! Perfect for families & large groups. I built and designed my home it's b ...
From $853 per night (USD)
VRBO
From $91 per night (USD)
VRBO
Private Room + Bathroom In Historic Luxury Loft w Skyline Views & Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This historic converted 2 Bedroom loft space features 270 degree views of Chicago with nearly 20 foot ceilings and a pri ...
From $91 per night (USD)
VRBO
From $1002 per night (USD)
VRBO
Spacious Apartments for Groups w/ Skyline Views
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
Summary: 'The Tribune' is ideal for family and friends visiting West Loop’s best. Our first group of 2025 left a perfe ...
From $1002 per night (USD)
VRBO

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