Chicago Rentals
From $381 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 nei ...
From $381 per night (USD)VRBO
From $361 per night (USD)VRBO
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 spacio ...
From $361 per night (USD)VRBO
From $257 per night (USD)VRBO
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 ...
From $257 per night (USD)VRBO
From $275 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 hom ...
From $275 per night (USD)VRBO
From $263 per night (USD)VRBO
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 $263 per night (USD)VRBO
From $376 per night (USD)Expedia
3BR | Complete & Well-Located Apt in Hyde Park
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Spacious and comfortable 3BR apartment in the heart of Hyde Park. This fully equipped and thoughtfully furnish ...
From $376 per night (USD)Expedia
From $266 per night (USD)VRBO
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 Lay ...
From $266 per night (USD)VRBO
From $372 per night (USD)Expedia
Modern 4BR Rogers Park Stay Near Loyola
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Gather your group and enjoy a comfortable Chicago stay just minutes from Loyola University, Lake Michigan beac ...
From $372 per night (USD)Expedia
From $665 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 $665 per night (USD)VRBO
From $321 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 $321 per night (USD)Expedia
From $271 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 $271 per night (USD)VRBO
From $1738 per night (USD)Expedia
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 $1738 per night (USD)Expedia
From $581 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' ...
From $581 per night (USD)VRBO
From $401 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 $401 per night (USD)Expedia
From $613 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 $613 per night (USD)VRBO
From $292 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. ✦ Cl ...
From $292 per night (USD)Expedia
From $676 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 $676 per night (USD)VRBO
From $256 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. ✦ Cl ...
From $256 per night (USD)Expedia
From $342 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. ✦ Cl ...
From $342 per night (USD)VRBO
From $589 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 $589 per night (USD)Expedia
From $512 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 $512 per night (USD)VRBO
From $302 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. ✦ Cl ...
From $302 per night (USD)Expedia
From $321 per night (USD)VRBO
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 $321 per night (USD)VRBO
From $303 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 $303 per night (USD)VRBO
From $207 per night (USD)VRBO
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 $207 per night (USD)VRBO
From $785 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 $785 per night (USD)VRBO
From $426 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 $426 per night (USD)VRBO
From $290 per night (USD)Expedia
Spacious 2BR - 10 mins from Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your home away from home in Chicago — just 10 minutes from downtown! We’re conveniently located right by the ...
From $290 per night (USD)Expedia
From $197 per night (USD)VRBO
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 $197 per night (USD)VRBO
From $202 per night (USD)Expedia
1 GB Wi-Fi, 1 Reserved Parking Space, Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Stay in this modern 1BR, 1BA apartment in Lakeview, Chicago, perfect for families, friends, or groups of up to ...
From $202 per night (USD)Expedia
From $300 per night (USD)VRBO
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 la ...
From $300 per night (USD)VRBO
From $274 per night (USD)Expedia
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 $274 per night (USD)Expedia
From $138 per night (USD)VRBO
Modern 2BR Apartment in Medical District
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy your stay in this spacious, fully furnished 2-bedroom, 1.5-bath apartment in Chicago’s Medical District. With two ...
From $138 per night (USD)VRBO
From $283 per night (USD)VRBO
2 Comfortable Suites Perfect for Families & Groups
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $283 per night (USD)VRBO
From $149 per night (USD)VRBO
O'Hare Suite Perfect for Families w/ Free Breakfast & Onsite Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $149 per night (USD)VRBO
From $278 per night (USD)VRBO
2 Clean Suites Ideal for Groups & Families + Convenient Airport Access Nearby
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $278 per night (USD)VRBO
From $149 per night (USD)VRBO
Contemporary Suite Near Rosemont Theater, w/ Free Breakfast & Onsite Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $149 per night (USD)VRBO
From $278 per night (USD)VRBO
Relax in 2 Family-Friendly Suites w/ Heated Pool & Hot Breakfast Near Airport
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $278 per night (USD)VRBO
From $149 per night (USD)VRBO
Enjoy A Clean & Quiet Suite w/ Kitchenette & Pool | Minutes from O'Hare Airport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $149 per night (USD)VRBO
From $283 per night (USD)VRBO
Experience Quiet Comfort in 2 Family-Friendly Suites w/ Pool & Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $283 per night (USD)VRBO
From $149 per night (USD)VRBO
Modern Suite w/ Free Breakfast & Onsite Pool Near Cumberland CTA Station
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $149 per night (USD)VRBO
From $348 per night (USD)Expedia
Wrigleyville Retreat • 1BR • Sleeps 6 • Full Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Ruby's Garden is a modern 1BR Near Wrigley Field • 1 Block from the Stadium Sleeps 6 • Full Kitchen • AC • Perfect for S ...
From $348 per night (USD)Expedia
From $175 per night (USD)VRBO
Cozy Streeterville Corner Unit
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Corner unit with open views in Streeterville. Spacious junior 1 bedroom just one block west of the lake and steps from t ...
From $175 per night (USD)VRBO
From $428 per night (USD)Expedia
Bright 3 BR Wicker Park Loft. 5Beds + 2 parking. 4-min walk to Damen Blue Line!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your bright, design-forward home base in the heart of Wicker Park. This spacious 3-bedroom retreat sleeps gro ...
From $428 per night (USD)Expedia
From $817 per night (USD)VRBO
Beautiful, Spacious 3BR Ukrainian Village Home w/ Deck, Garage & Room for Groups
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to a spacious, beautifully furnished home in the heart of Ukrainian Village, designed for families, groups, wedd ...
From $817 per night (USD)VRBO
From $327 per night (USD)Expedia
Your Logan Square Oasis with Lush Outdoor Haven!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Catalpa Court -- located in the heart of Chicago's beautiful Logan Square neighborhood :) Bright and spaciou ...
From $327 per night (USD)Expedia
From $465 per night (USD)VRBO
The Brass Key Residence
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Step into The Brass Key Residence, a thoughtfully curated vintage-inspired home filled with antique treasures, timeless ...
From $465 per night (USD)VRBO
From $1329 per night (USD)Expedia
Massive Queen Anne Mansion for your whole family to stay!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 15
This is your chance to stay in a historic Chicago mansion. This beautiful Queen Anne style mansion has an abundance of c ...
From $1329 per night (USD)Expedia
From $420 per night (USD)VRBO
Designer Loft 4E | Heart of Gold Coast/River North
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Summary: BRAND NEW APARTMENT IN THE HEART OF RIVER NORTH & GOLD COAST! Enjoy your designer styled unit located in Ch ...
From $420 per night (USD)VRBO
From $422 per night (USD)Expedia
Designer Loft 3E | Heart of Gold Coast/River North
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: BRAND NEW APARTMENT IN THE HEART OF RIVER NORTH & GOLD COAST! Enjoy your designer styled unit located in Ch ...
From $422 per night (USD)Expedia
From $368 per night (USD)VRBO
Spacious Apt | 4 Queen Beds | Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Modern Chicago apartment in a quiet residential neighborhood, perfect for 8 guests. Features a full kitchen, high-speed ...
From $368 per night (USD)VRBO
From $1756 per night (USD)Expedia
Bohome Reserve: Chicago Wicker Park • Sauna • Chef's Kitchen • Outdoor Lounging
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Designer, plant-infused 4BR/3.5BA home in Wicker Park—crafted for retreat, work, and play. Unwind in the private sauna, ...
From $1756 per night (USD)Expedia
From $478 per night (USD)VRBO
Spacious 4BR; 2.5BR; en-suite;FL basement;appliances;central air& heat included!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Make yourself at home in this 4-bedroom Chicago townhome retreat. Each bedroom features a comfortable queen bed, perfect ...
From $478 per night (USD)VRBO
From $556 per night (USD)Expedia
4BR Downtown Retreat | Free Street Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Charming Chicago retreat in quiet Bridgeport. This modern 4-bedroom apartment, featuring queen beds, 2 full baths, and a ...
From $556 per night (USD)Expedia
From $336 per night (USD)VRBO
Ravenswood Loft - Peaceful 2-bedroom apartment in vibrant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Charming 2BR in Ravenswood Manor! This cozy, sunlit apartment sleeps 6 and features 2 bedrooms, 1 bath, a full kitchen, ...
From $336 per night (USD)VRBO
From $416 per night (USD)Expedia
Large and conveniently located
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Chicago, enjoy what this 3-bedroom apartment has to offer. The space features one king bed and two queen beds ...
From $416 per night (USD)Expedia
From $661 per night (USD)VRBO
Stay at The Velvet Manor, a beautifully designed 3BR home just steps from Andersonville's vibrant Clark Street. Enjoy spacious living, a chef's kitchen, dedicated office, Jacuzzi tub, outdoor area, and garage parking.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Velvet Manor, a moody, designer-curated 3-bedroom retreat in the heart of Andersonville. Unwind in richly ...
From $661 per night (USD)VRBO
From $696 per night (USD)Expedia
Arcade • Theater • Gym • Office • Sleeps 15
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 15
Welcome to Giddings Chicago 985 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...
From $696 per night (USD)Expedia
From $458 per night (USD)VRBO
Charming Historic Row Home in Lincoln Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience historic charm and modern luxury in the heart of Lincoln Park. This updated 1870s row home features a privat ...
From $458 per night (USD)VRBO
From $265 per night (USD)Expedia
Spacious 3-bedroom Comfort Urban Chicago loft house
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your cozy getaway awaits in Chicago at this marvelous apartment. With three bedrooms featuring a queen, full, and twin b ...
From $265 per night (USD)Expedia
From $548 per night (USD)VRBO
Wonderful townhome East Lakeview near cubs 5 min walk to lake in vibrant Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This memorable townhome is the perfect home base for your trip to Chicago. Guests will find three comfortable bedrooms, ...
From $548 per night (USD)VRBO
From $550 per night (USD)Expedia
Newly Renovated 3BR/3BA Single Family Home Steps to Pool, Parks and River Trail
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
*3 month minimum stays only* Welcome to your Chicago home away from home! This beautifully reimagined 3-bedroom, 3-bath ...
From $550 per night (USD)Expedia
From $325 per night (USD)VRBO
2BR Avondale Apt: Free Parking + Steps to Blueline
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in a modern 2 Bedroom Apartment that sleeps 6 in a peaceful setting, just minutes from downtown and Logan Square—st ...
From $325 per night (USD)VRBO
From $158 per night (USD)Expedia
Fully Furnished 2BR. 5-min walk to train. In-unit laundry. Parking Available
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Rental Month-to-month rental with option for longer lease. Discover your perfect urban retreat in the heart of Chicag ...
From $158 per night (USD)Expedia
From $296 per night (USD)VRBO
2 bedroom apartment near University of Chicago and Obama Center for your stay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stay in a stylish, private-entry 2-bedroom garden apartment in Chicago’s historic Woodlawn neighborhood, while you visit ...
From $296 per night (USD)VRBO
From $298 per night (USD)Expedia
Hyde Park/ Bronzeville Apartment 3E
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This spacious 3-bed apartment in the Bronzeville area is the center of everything that you'll need while staying here. J ...
From $298 per night (USD)Expedia
From $220 per night (USD)VRBO
Luxury 1BR Chicago Retreat downtown Free Parking, Gym, Theater & Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Your Chicago Getaway Welcome to your stylish and comfortable 1-bedroom, 1.5-bathroom Chicago retreat, desig ...
From $220 per night (USD)VRBO
From $409 per night (USD)Expedia
Sweet Home Chicago- 3 BR, 2.5 BA + Game Room, Hot Tub, near O'Hare, Rosemont
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the beauty of Chicago from this unique Chicago inspired 3-bedroom house. Inside, guests find a queen bed, two t ...
From $409 per night (USD)Expedia
From $254 per night (USD)VRBO
Quiet Stay - Perfect for Family
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Indulge in the charm of urban living at our inviting short-term rental property, where comfort and convenience blend sea ...
From $254 per night (USD)VRBO
From $671 per night (USD)Expedia
2-bedroom apartment in perfect Chicago with cool AC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Your Chicago adventure begins at this 2-bedroom apartment. Step into a serene space where cool air flows through the roo ...
From $671 per night (USD)Expedia
From $247 per night (USD)VRBO
Quiet Area - Revamped Basement
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your cozy retreat! Our 2-bedroom short-term rental is designed to offer you a comfortable and convenient stay ...
From $247 per night (USD)VRBO
From $290 per night (USD)Expedia
Stylish friendly 3BR Suite near McCormick
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
🌆 Experience Downtown Comfort at The State Suite — Your Premier Chicago Stay! Wake up in the heart of Chicago at The S ...
From $290 per night (USD)Expedia
From $307 per night (USD)VRBO
McCormick 4BR Huge Unit w/ Pool Table | Sleeps 11
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Relax with the whole family or your group at this spacious and comfortable retreat in the heart of Chicago! 📣 MESSAGE ...
From $307 per night (USD)VRBO
From $246 per night (USD)Expedia
Spacious 3BR Smoke Ok | McCormick & UIC Campus
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
🌆 Welcome and Step into the perfect blend of style, comfort, and city energy at the State Suite, your urban retreat in ...
From $246 per night (USD)Expedia
From $241 per night (USD)VRBO
South Loop 3BR Smoke Ok Suite Near McCormick
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
🌆 Welcome and Step into The State Suite, where city sophistication meets home-like comfort in the heart of downtown Chi ...
From $241 per night (USD)VRBO
From $574 per night (USD)Expedia
Lovely three bedroom Loft, University Of Chicago, Obama Library
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The property boasts an open and inviting floor plan, flooded with natural light, and luxurious finishes throughout, such ...
From $574 per night (USD)Expedia
From $169 per night (USD)VRBO
Beautiful Condo in the Middle of Andersonville
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Walking Distance to Public Transit | Private Back Porch | In-Unit Laundry Experience Chicago like a local in the heart ...
From $169 per night (USD)VRBO
From $1764 per night (USD)Expedia
Perfect 5-bedroom estate in vibrant Chicago.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 15
Stay comfortably in Chicago at this amazing 5-bedroom estate. With a king bed, four queen beds, a twin bed, and a sofa b ...
From $1764 per night (USD)Expedia
From $362 per night (USD)VRBO
NEW! Fully Updated Jr. 1 Bed, Steps from Lincoln Park by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
My bright and stylish Jr. 1-bed, 1-bath condo is located in a prime Lincoln Park location. Thoughtful touches can be fe ...
From $362 per night (USD)VRBO
From $488 per night (USD)Expedia
The Velvet Manor | 2BR Boutique Stay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Velvet Manor, a moody, designer-curated 2-bedroom retreat in the heart of Andersonville. Unwind in richly ...
From $488 per night (USD)Expedia
From $116 per night (USD)VRBO
Private Basement Suite-Completely separate from the rest of the house
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Spacious & Comfortable Chicago Stay Near 95th Red Line | Fast Wi-Fi | Free Parking | Monthly Discounts Welcome to your ...
From $116 per night (USD)VRBO
From $140 per night (USD)Expedia
3bd/2ba, King bd, Pets OK, Laundry, Fenced Yard, Near Downtwn, Hospitals, & Unis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Rental Terms: Minimum stay: 30 nights If this home doesn't suit your needs, message me. We have other homes available i ...
From $140 per night (USD)Expedia
From $276 per night (USD)VRBO
LIVN West Loop Chicago Classic Queen Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Experience modern city living at LIVN West Loop Chicago, a stylish studio at 555 W Jackson Blvd in one of Chic ...
From $276 per night (USD)VRBO
From $246 per night (USD)Expedia
LIVN Millennium Park Downtown Chicago Superior 1BR
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Experience the best of Chicago from this stylish, newly renovated 1 bedroom at 19 S Wabash Ave. Perfectly loca ...
From $246 per night (USD)Expedia
From $246 per night (USD)VRBO
LIVN Millennium Park Downtown Chicago Prem Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Experience the best of Chicago from this stylish, newly renovated premium studio at 19 S Wabash Ave. Perfectly ...
From $246 per night (USD)VRBO
From $246 per night (USD)Expedia
LIVN West Loop Chicago Queen Superior Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Experience modern city living at LIVN West Loop Chicago, a stylish studio at 555 W Jackson Blvd in one of Chic ...
From $246 per night (USD)Expedia
From $223 per night (USD)VRBO
LIVN Millennium Park Downtown Chicago Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Experience the best of Chicago from this stylish, newly renovated studio at 19 S Wabash Ave. Perfectly located ...
From $223 per night (USD)VRBO
From $273 per night (USD)Expedia
LIVN Millennium Park Downtown Chicago Superior 2 BR
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience the best of Chicago from this stylish, newly renovated 2-bedroom at 19 S Wabash Ave. Perfectly loca ...
From $273 per night (USD)Expedia
From $223 per night (USD)VRBO
LIVN Millennium Park Downtown Chicago 1 BR
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Experience the best of Chicago from this stylish, newly renovated 1-bedroom at 19 S Wabash Ave. Perfectly loca ...
From $223 per night (USD)VRBO
From $255 per night (USD)Expedia
Beautifully Remodeled 2B/2BA Hyde Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Requires walking up 2 flights of stairs. Enjoy your stay in this charming 2 bed, 1 bath apartment in the heart of Hyde ...
From $255 per night (USD)Expedia
From $411 per night (USD)VRBO
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to Reserve Chicago 358 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ No ...
From $411 per night (USD)VRBO
From $467 per night (USD)Expedia
Peaceful Zen Flat | 2BR Oasis with Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Escape to this bright, luxe West Town retreat designed to feel like your own boutique city hideaway. Nestled on a quiet, ...
From $467 per night (USD)Expedia
From $419 per night (USD)VRBO
Zen City Escape | Patio + Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to your Zen City Escape. This bright top-floor retreat offers free onsite parking, a private patio, and thoughtf ...
From $419 per night (USD)VRBO
From $359 per night (USD)Expedia
LIVN West Loop Chicago King Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Experience modern city living at LIVN West Loop Chicago, a stylish king studio at 555 W Jackson Blvd in one of ...
From $359 per night (USD)Expedia
From $448 per night (USD)VRBO
LIVN West Loop Chicago 2 BR City View
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience modern city living at LIVN West Loop Chicago, a stylish 2 bedroom at 555 W Jackson Blvd in one of C ...
From $448 per night (USD)VRBO
From $267 per night (USD)Expedia
LIVN West Loop Chicago 1 BR
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Experience modern city living at LIVN West Loop Chicago, a stylish 1 BR at 555 W Jackson Blvd in one of Chicag ...
From $267 per night (USD)Expedia
From $254 per night (USD)VRBO
LIVN Millennium Park Downtown Chicago 2BR
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience the best of Chicago from this stylish, newly renovated 2-bedroom at 19 S Wabash Ave. Perfectly loca ...
From $254 per night (USD)VRBO
From $255 per night (USD)Expedia
Retreat Near Andersonville 3BR Newly Remodeled
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Requires walking up 2 flights of stairs. Enjoy your stay in this beautifully updated 3-bedroom, 2-bath apartment near t ...
From $255 per night (USD)Expedia
From $176 per night (USD)VRBO
Your Parkside Executive Retreat + Dedicated Office
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Superb Executive Housing, a quiet and comfortable home away from home near historic Pullman and directly acro ...
From $176 per night (USD)VRBO
From $213 per night (USD)Expedia
Boulevard Stays River North Retreat Near Magnificent Mile 01
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Walk to the best of River North, with the Magnificent Mile, Chicago Riverwalk, Merchandise Mart, and CTA Red L ...
From $213 per night (USD)Expedia