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Apartment Rentals and Condos in Chicago, IL

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    Travelers to Chicago are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 18
    Lakeview
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 26
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 8
    West Town
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 18
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Want to live like a local while staying in Chicago and save? Reserve now and take advantage of fall savings! Our Chicago vacation rental offers an affordable and comfortable place to lay your head during your visit to our city! A family-owned, Chicago boutique property near Wrigley Field, The... View all property information
    Location Information
    Chicago, Illinois 60640
    1 / 11
    Northwest Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Ref # 361759 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Enjoy tranquil moments in this furnished two bedroom condo in Chicago. This unit has... View all property information
    Location Information
    Chicago, Illinois 60630
    1 / 34
    3.5 of 5 bubbles (2) Average
    Rogers Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Nice and bright 2 bedroom 2 full bathrooms condominium, two blocks from the lake and one block from train, bus, restaurants and coffee shops. Unit is cozy, spacious and conveniently located on first floor, washer and dryer. Hardwood floors. LOCATION: The unit is located on East Rogers Park, two... View all property information
    Location Information
    Chicago, Illinois 60626
    1 / 9
    West Town, Wicker Park / Bucktown
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Art + design geeks will enjoy this clean, welcoming, open space filled with designer/modern/classic/smart home elements. Message me to confirm availability. This is where I spend most of my time (sleeping, working, lounging, etc) so it's a bit tricked out to suit my own liking, but perhaps you'll... View all property information
    Location Information
    Chicago, Illinois 60647
    1 / 18
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Ref # 360390 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Live in this nice and comfy 2 bedroom, 1 bathroom fully furnished apartment in Chicago.... View all property information
    Location Information
    Chicago, Illinois 60647
    1 / 8
    Lincoln Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    This house is ideal for a weekend visit or long stay. Every amenity is at your fingertips and every Chicago site is steps or a train away. Great modern space with eat-in chefs kitchen updated comfortable bathrooms and spacious city backyard. Perfect location for a Chicago getaway!!! Heart of... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 7
    5 of 5 bubbles (4) Excellent
    Near North Side
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Our newly rehabbed and fully furnished unit has 4 bedrooms, 2 bathrooms and sleeps 10. Whether you are planning a weekend excursion, business trip or need a comfortable place to stay for family or friends. We are in a great family neighborhood close to downtown. You can walk to the Zoo and North... View all property information
    Location Information
    Chicago, Illinois 60614
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    1 / 19
    5 of 5 bubbles (1) Excellent
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Choose from Studio, Jr. One Bedroom, One Bedroom and upgraded One Bedroom + Den apartments. An on-site pool highlights this modern apartment in Chicago's theatre district. The property is 1,650 feet from iconic Willis Tower and just 10 minutes' walk from Millennium Park. Check out live shows at... View all property information
    Location Information
    Chicago, Illinois 60606
    1 / 14
    Lakeview
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    This renovated apartment is in an oasis while enjoying all the excitement that Wrigleyville and Chicago have to offer! Walk to Wrigley Field, CTA Red Line, nightlife, bars, restaurants and more! Lots of space in an awesome location - and a beautiful space! With three bedrooms, each with it's own... View all property information
    Location Information
    Chicago, Illinois 60613
    1 / 52
    4.5 of 5 bubbles (11) Very good
    DePaul
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    BEFORE YOU BOOK PLEASE NOTE THERE IS A 4 NIGHT MINIMUM FROM MAY THROUGH OCTOBER, WITH A 5 NIGHT MINIMUM FOR HOLIDAY WEEKENDS AND SPECIAL EVENT WEEKENDS. PLEASE DO NOT AUTOBOOK FOR PERIODS SHORTER THAN WHAT IS REQUIRED AS THE BOOKING WILL NOT BE HONORED. PLEASE EMAIL OR CALL WITH ANY QUESTIONS.... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 13
    Lincoln Park
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Our place is a brand new renovation! You'll love the kitchen, the location, and the coziness. Perfect for couples, solo adventurers, and business travelers. The Victorian row house with the red door is located in the heart of Lincoln Park & walking distance to lots to enjoy (see photos). Our... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 8
    Roscoe Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Located in the Heart of Roscoe Village--"A village within the city." Trendy Roscoe Village offers a variety of boutiques, restaurants and bars. We are approximately 7 blocks from the Paulina brown stop, which will take you downtown in approximately 15 minutes. We are also located a short... View all property information
    Location Information
    Chicago, Illinois 60618
    1 / 16
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Just a couple blocks from the United Center this splendidly rehabbed 3 story townhouse is the place for your group to stay when visiting Chicago. Plenty of space for everyone! Full kitchen and dining room. 4 Bedrooms, and an additional two sleeper sofas. 2.5 Baths and two big living areas. Garage... View all property information
    Location Information
    Chicago, Illinois 60612
    1 / 16
    Near North Side
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    A rare opportunity to stay in Chicago's most prominent neighborhood! This fabulous apartment features 2 bedrooms and 1 bathroom, bright and spacious living room with a designated dining room. The kitchen comes fully equipped with dinnerware, flatware, pots and pans, french press coffee makers,... View all property information
    Location Information
    Chicago, Illinois 60610
    1 / 19
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Ref # 365218 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. This building is located in Chicago's West Loop neighborhood situated near the... View all property information
    Location Information
    Chicago, Illinois
    1 / 20
    Lakeview
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    This 5 bedroom apartment sleeps 14, an oasis in the midst of all the excitement that Wrigleyville and Chicago have to offer! Walk to Wrigley Field, CTA Red Line, nightlife, bars, restaurants, and lots more! Perfect for families and large groups! Lots of space in an awesome location - and a... View all property information
    Location Information
    Chicago, Illinois 60613
    1 / 18
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Unit not available for daily rental in July 4th Holiday !<BR><BR><BR>*Prices may vary depending on the season. Premium months are between April and September. <BR>*Prices negotiable based on length of stay. Please inquire and we will provide a direct quote for your stay.<BR><BR><BR>High-end,... View all property information
    Location Information
    Chicago, Illinois 60601
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    1 / 21
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Live like a Chicago local in luxury - the perfect location to take in downtown Chicago! Great for McCormick Place meetings - 10 min away! Easy access to Soldier Field, Museum Campus, Grant Park, Magnificent Mile, and steps from the L! Enjoy the perfect home-base for exploring Chicago for you and... View all property information
    Location Information
    Chicago, Illinois 60605
    1 / 7
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Welcome to the American Eagle -- the perfect combination of powerful performance and stylish comfort. On the road, you'll enjoy an exceptional driving experience in a luxurious cockpit with Ultraleather™ seats and a wide range of state- of-the-art features. Specifications: -solar panel -15K lb.... View all property information
    Location Information
    Chicago, Illinois 60446
    1 / 5
    West Town, Wicker Park / Bucktown
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Remember John Cusack's movie, High Fidelity? This would have been his dream Wicker Park apartment - right above Reckless Records, in the best part of the neighborhood - steps from the best bars, restaurants, shopping, the Blue Line el. Gorgeously appointed, a full European steam shower. This... View all property information
    Location Information
    Chicago, Illinois 60622
    1 / 19
    Lakeview
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Luxury Wrigleyville Vacation Rental Condo - 4 Bedroom / 3 Bath / Sleeps 12 - 3 Blocks from Wrigley Field - Newly Constructed Building - High End Luxury Finishes - 1st floor unit, 2 level, duplex down. Sleeps up to 12 with the addition of 2 queen size air mattresses. - 3 - 50' plasma tvs,... View all property information
    Location Information
    Chicago, Illinois 60657
    1 / 15
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Exclusive tower location, feet from The Bean and the Loop L Train! Local guidebook telling you what to hit and skip! We're from Chicago. We live here. We know the place, and we have an opinion! This is your best option for an amazing base to explore Chicago, with 9 others! This is the BEST... View all property information
    Location Information
    Chicago, Illinois 60602
    1 / 18
    Northwest Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Luxurious and fully furnished apartment available for a short-term lease of up to three months. Dates are flexible! Ideal for corporate/business travelers looking for a unique experience! Convenient to public transportation. A cozy, beautiful and vintage-drenched storefront apartment ideally... View all property information
    Location Information
    Chicago, Illinois 60622
    1 / 14
    Northwest Side
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Wrap up 2015 and get the New Year off to a great start by making this 1800 sq ft condo your new home! Fully furnished, all utilities included, HBO, High Speed Internet...Everything is ready to go. When considering real estate, everyone has heard that the only three factors that matter are... View all property information
    Location Information
    Chicago, Illinois 60642
    1 / 19
    Lakeview
    6 Bedrooms, 2 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Lots of space in an awesome location - ONE BLOCK FROM WRIGLEY FIELD AND THE CHICAGO CUBS! This apartment sleeps 16 GUESTS over TWO FLOORS! It offers five queen beds and one double bed in their own bedrooms, plus in the semi-private alcoves in common spaces we have two queen beds, as well as two... View all property information
    Location Information
    Chicago, Illinois 60613
    1 / 25
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    This historic turn of the century home has been recently remodeled while paying homage to original and period details like crown moldings and stained glass. Fresh, clean and sparkling with drop dead mid century décor. Both comfortable, roomy and stylish. There is a large fully stocked kitchen with... View all property information
    Location Information
    Chicago, Illinois 60625
    1 / 31
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Unit not available for daily rental in July 4th Holiday !<BR><BR><BR>*Prices may vary depending on the season. Premium months are between April and September. <BR>*Prices negotiable based on length of stay. Please inquire and we will provide a direct quote for your stay.<BR><BR><BR>30 days minimum... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 40
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Ref # 369697 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. If you are looking for a spacious 2,000sq fully furnished condo with brand new floors,... View all property information
    Location Information
    Chicago, Illinois 60653
    1 / 7
    5 of 5 bubbles (1) Excellent
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Top floor unit in historic Old Town Neighborhood. Close to shopping, Brown Line El stop. Downtown . And North Avenue Beach! We do allow 1-2 nights stays Monday-Thursday with a cleaning fee. Over any weekend we have minimum nights stay of 3,4,5 or 6 nights. Please ask how many nights your... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 17
    Southwest Side
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Experience top quality in a spacious apt during your next visit to beautiful Chicago!. Features 2 bedroom & 2 bathroom with 2 separate living rooms, gourmet kitchen and laundry room. Located in quiet neighborhood only 10 mins away from the heart of downtown for an affordable price The spacious... View all property information
    Location Information
    Chicago, Illinois 60609
    1 / 20
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    • Central Heating
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    About this property
    Booked through May 1. Thank you! Enjoy a great urban experience staying in The ALONZO HOUSE, an amazing art filled loft in the Ukrainian Village, Chicago's 1st Ward. This beautiful three story Victorian house was built in 1885, in the heart of Ukrainian village/West town, one of the oldest... View all property information
    Location Information
    Chicago, Illinois 60622
    1 / 14
    Lakeview
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Stunning, contemporary and flawlessly designed single family home in Chicago’s Lakeview neighborhood. The residence boasts 5000 sq feet of indoor and outdoor living, featuring top of the line finishes and furnishings, including granite and stainless steel in a gorgeous chef’s kitchen with Viking... View all property information
    Location Information
    Chicago, Illinois 60657
    1 / 22
    5 of 5 bubbles (6) Excellent
    DePaul
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This Unit has one regular sized bedroom and a "Lil" bedroom - twin bed only. The second bedroom is tiny and I want to make certain you understand that before booking. Please look at the photos - there's a window, some shelves, a twin bed. The door is just off the kitchen and the AC unit is located... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 11
    4.5 of 5 bubbles (4) Very good
    Roscoe Village
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Trendy Roscoe Village offers a variety of boutiques, restaurants and bars. Our Guesthouse is located a block from Cinnamon Boutique, a new women's clothing and accessory store and one of many fantastic places to shop in the village. We are approximately 4.5 blocks from the Paulina brown stop,... View all property information
    Location Information
    Chicago, Illinois 60618
    1 / 32
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Right in the heart of Chicago's premier Streeterville neighborhood. Famous landmarks such as Michigan Ave, Navy Pier, Millennium Park and Magnificent Mile are a short stroll away. Excellent location coupled with luxury living at its finest. Suite Details King bed in Master Bedroom and Queen Size... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 7
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Suite Home Chicago at Grand Plaza offers fully furnished apartments. Rates include housekeeping, all taxes, high speed wireless internet, expanded cable, all utilities, linens, towels, and first class customer service. Situated in the middle of the very popular River North neighborhood, Grand... View all property information
    Location Information
    Chicago, Illinois 60654
    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
    • x
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    About this property
    Welcome to our modern, comfortable apt. We are conveniently located blocks from Pink Line train. We live in a fantastic neighborhood full of art, great food and many convenient grocery stores. 5 minutes from Rush Hospital on Pink line train. Our neighborhood has a family friendly vibe full of art... View all property information
    Location Information
    Chicago, Illinois 60608
    1 / 10
    Lakeview
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    PLEASE NOTE: This is not a new property. We have recently left our previous management company, which had been managing this and our other 6 properties for 2+ years. Please see photos for past reviews! Our updated Lincoln Park apartment features: 4 bedrooms and 2 baths Sleeping for 8 Premier... View all property information
    Location Information
    Chicago, Illinois 60657
    1 / 20
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Live like a Chicago local in luxury - the perfect location for tourists to take in the downtown Chicago sights! Easy access to Soldier Field, Museum Campus, Grant Park, Magnificent Mile, and steps from the L! 10 min from McCormick Place! Enjoy the perfect home-base for exploring Chicago for you... View all property information
    Location Information
    Chicago, Illinois 60605
    1 / 12
    Near North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Modern 3 story townhouse with private penthouse to Garden Roof Top. Designer Town House has 100% Brazilian Cherry wood floors onyx fire place ,deisigner kitchen-stainless steel applicances/garnite counters/built in kitchen seating area with convenient outdoor balcony equipped with grill/seating for... View all property information
    Location Information
    Chicago, Illinois 60610
    1 / 4
    Roscoe Village
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • ?
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    • x
    About this property
    Brand new 4 bedroom 2 bath fully furnished apartment in Roscoe Village close to Hamlin Park. Whether you are planning a weekend excursion, business trip or need a comfortable place to stay for family or friends, consider our newly rehabbed Guesthouse on Leavitt St. We do allow 1-2 nights stays... View all property information
    Location Information
    Chicago, Illinois 60618
    1 / 11
    2 of 5 bubbles (1) Poor
    Rogers Park
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
    About this property
    The Space Living room and dining room combo. Rooms are nice and cozy, cute and quiet. The unit is located in the East Rogers Park neighborhood of Chicago and border with Edgewater, within walking distance to the CTA Red Line Loyola station, Loyola University, restaurants, coffee shops, Lake... View all property information
    Location Information
    Chicago, Illinois 60626
    1 / 11
    DePaul
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Internet Access
    • Patio
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    • Balcony
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    The Aster House has been a legitimate business since 1891 (!) and under the present owners since 1982. We've had tenants stay as long as 9 years and return for as long as 18 years, so you may be assured of a secure and comfortable stay! In fact, most of our business is thru repeats or referrals!... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 6
    Near South Side
    2 Bedrooms, 2 Bathrooms, Sleeps 3 | Quick View
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    • x
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    • x
    About this property
    A nice place to stay in the heart of Chicago. Beautiful home in a very convenient location. Lots of transportation, food, and entertainment, right at your fingertips. The home is also located within walking distance of McCormick Place, so if you're coming in town for a convention, this is place for... View all property information
    Location Information
    Chicago, Illinois 60616
    1 / 6
    3 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Very clean and cozy 3 bedrooms 1 bath home 2 of the bedrooms have queen-size beds 3rd room is used as a TV room but can be used for sleeping as well. Located 2 blocks from public trans 2 blocks from I 94 freeway. UBER trans to all tourist spots $10.-12.dollars all residential neighbor free... View all property information
    Location Information
    Chicago, Illinois 60619
    1 / 5
    Near North Side
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Shared Outdoor Pool...
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    • x
    • x
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    • x
    About this property
    Looking for luxury apartments in Chicago? Look no further than my 2 Bedroom unit, located in Chicago's highly desired Gold Coast neighborhood. Features include a swimming pool with a sundeck, fitness room, valet dry cleaners, business center with Wi-Fi, laundry facility. RED LINE TRAIN NEXT DOOR.... View all property information
    Location Information
    Chicago, Illinois 60610
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    All new remodeled in 2015 this modern apartment sits right outside the heart of Chicago. Private bedroom located on 3rd floor, has a queen size bed, a closet inside and computer table. Bathroom is shared. My place is close to public transport, the city center, parks, art and culture, and the... View all property information
    Location Information
    Chicago, Illinois 60609