Condo vacation rentals in Rogers Park, Chicago

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Popular amenities for Rogers Park, Chicago condo rentals

Weekly condo rentals

Guest favourite
Condo in West Town
4.96 out of 5 average rating, 52 reviews

NEW! Spacious Modern 5 BD Condo

MichelleRating, 5 stars1 month ago
Great place for our Chicago spring break trip. House photos were current, it had listed amenities, and was 2 blocks walk to the Blue line and plenty of shops/restaurants were walking distance. Nice neighborhood close to the action. I would note a few things for people considering this house : 1) Parking was readily available near the unit during daytime hours, but was trickier in the evenings/weekends. We did (eventually) always find a spot somewhere nearby when we drove places. 2) Layout of bedrooms is: main floor king bedroom with private shower bathroom; main floor queen, main floor full bath. Basement has other king, two queen rooms, and other full bathroom. 3) The quiet hours in the rules make even more sense when you realize this unit is 1st/basement and someone else (with little kid(s) lives on 2/3. It worked well for us since we had kids with us too so our noisy times were mostly in sync. 4) Ally was super responsive when we had questions or issues. A+ for that!
Superhost
Condo in Wicker Park
4.84 out of 5 average rating, 184 reviews

Loft-Like Wicker Park Condo Steps from the Cta!

KathyRating, 5 stars1 month ago
Great place! Very well kept and clean. Tom is very responsive from the time you book. Just be mindful that as stated there is NO where to park if you drive. All in all such a great neighborhood.
Top guest favourite
Condo in West Town
4.92 out of 5 average rating, 261 reviews

Modern/Spacious 2BR/2BA West Town

AlexRating, 5 starstoday
Our stay at Charissa's condo was perfect for our short but full stay in Chicago. We enjoyed the walk to the L Train and the neighborhood around it, and the space itself was accommodating and even luxurious when it came to the bathrooms. The instructions were not complicated for accessing the condo, the space was well kept, and we had no trouble seeing it as a main staple of our amazing weekend.
Superhost
Condo in Logan Square
4.79 out of 5 average rating, 251 reviews

Logan Square Beauty with 2 Bedrooms W/parking

SarahRating, 5 stars2 weeks ago
We really enjoyed our three nights in Matt's roomy upstairs apartment. Great to have a space in his garage; the car stayed parked there while we took the blue line downtown each day. It was an easy 10 minute walk to the Logan Square station. If you're flying into or out of O'Hare, it would be convenient, since the airport is the last stop on the blue line.
Guest favourite
Condo in Chicago
4.92 out of 5 average rating, 155 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

AllondaRating, 5 stars2 weeks ago
Eugene is an amazing host that is very communicative and flexible. This property looked just like the pictures, clean, safe and bigger than expected. The property is in walking distance of two amazing restaurants Taqueria Varitas and a breakfast place called peaches. 10/10 highly recommend!
Superhost
Condo in East Rogers Park
4.81 out of 5 average rating, 136 reviews

Marvelous Condo w/ Pri Prkng Cls to Transit &Beach

NicholasRating, 5 stars2 weeks ago
Very quick to respond to questions and great detailed instructions. The place was clean and comfortable! Awesome!
Guest favourite
Condo in Lincoln Park
4.95 out of 5 average rating, 489 reviews

Unique Lincoln Park Duplex Apt

JohnRating, 5 stars4 weeks ago
Very nice place. Everything was up-to-date and clean; nice bathroom with roomy shower; enjoyed the fireplace and liked having the bedroom upstairs from living area. Full grocery and two good restaurants just down the street, other good options within ten or fifteen minutes walk. Buses nearby and "L" trains 15 minutes away. Host was responsive and welcoming.

Pet-friendly condo rentals

Guest favourite
Condo in Pilsen Historic District
4.85 out of 5 average rating, 131 reviews

816 PLZN Luxury Apt | Rooftop | Garage Parking

SabrinaRating, 5 stars3 weeks ago
such a great lovely place to stay thank you for the great hospitality!
Guest favourite
Condo in Lincoln Square
4.93 out of 5 average rating, 115 reviews

The Fox Den

JamesRating, 5 stars3 weeks ago
This place was great from the balcony to the fenced in area behind the house. Parking was easy and free on the side streets. The retro appliances really stood out in the kitchen. Wonderful are for dogs to go out easily and safe to be able to walk them. A few parks nearby. Great place to stay with lots to do within walking distance.
Guest favourite
Condo in Chicago
4.89 out of 5 average rating, 112 reviews

Unique 2BR/2BA FREE Street Parking/WI-FI Near DT

JasonRating, 5 stars1 month ago
Wonderful, everything was clean and lots of fun stuff nearby I recommend anyone book here it’s a great stay
Superhost
Condo in The Loop
4.85 out of 5 average rating, 130 reviews

Downtown Mich Ave #7| Park View Penthouse +gym

ThanhRating, 5 stars2 weeks ago
Beautiful spot, cannot be be beat, was a block away from our favorite pizza spot and a few blocks from our dumpling place. The rooftop view is stunning, panoramic view of the city. As for the apt — it was very well laid out, maximizing all of the space and the softest couch we’ve had in any Airbnb to date. Hosts were in constant communication and we were only there for a long weekend university visit. Very happy with the place, would use again this summer or for any future visits to the city.
Guest favourite
Condo in East Rogers Park
4.92 out of 5 average rating, 233 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

JaredRating, 5 stars3 days ago
I always have the best time in Chicago, but Kaye’s place made this trip even better! I loved staying here so much, I actually extended my stay by a few days. Kaye has thought of everything, and to quote Tina Turner, she is “simply the best!” This is my favorite Airbnb I have ever stayed in and Kaye is the best host! I would recommend her place to all my friends and family. Can’t wait to visit again!
Top guest favourite
Condo in Logan Square
4.91 out of 5 average rating, 341 reviews

Susie's Space. 2BR easy parking & pet friendly

zenaRating, 5 stars5 days ago
Susan's place was a great affordable option for a cozy place that isn't too far from downtown! the local places around the unit were also super nice! The space was fairly cleaned and well organized. There's plenty of amenities that made the stay more comfortable.
Guest favourite
Condo in Wicker Park
4.88 out of 5 average rating, 261 reviews

Spacious & Stylish Home at the ♥ of Wicker Park

ZachariahRating, 5 stars1 month ago
Convenient location with lots of space
Top guest favourite
Condo in Lincoln Park
4.98 out of 5 average rating, 250 reviews

Pets OK | Walk Score 95 | Desk | 1,750ft² |W/D

KristinRating, 5 stars1 month ago
Great stay!! Perfect location and it suited our family and dogs wonderfully while we weee in Chicago for 4 nights. I passed this listing along to a friend who is looking to stay in the same area. Overall great experience and we loved our time there!

Condo rentals with a pool

Guest favourite
Condo in Downers Grove
4.92 out of 5 average rating, 62 reviews

Upscale, Washer Dryer, Smoke Free, Pet Free,

NormaRating, 5 stars4 months ago
My husband and I stayed here over the holidays. The apartment was pretty well appointed, clean and is in a good location- centrally located for our purposes of being near family and close enough to the expressway to get to the city.
Guest favourite
Condo in Evanston
4.96 out of 5 average rating, 95 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

PeteRating, 5 stars1 week ago
This condo is well appointed and stocked with coffee, creamer and seasonings. The building has a nice common area with fancy coffees and a decent work out room. We love the location near downtown Evanston and the public transportation to Chicago. We’ve stayed here many times and plan to stay here for all our Chicago visits.
Guest favourite
Condo in Evanston
4.95 out of 5 average rating, 105 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

JasonRating, 5 stars2 weeks ago
Our stay in Evanston was great! The apartment is close to all of downtown Evanston, the Metra, and the L. Also easy access to NU. Everything was just as it says and the free underground parking is a HUGE plus!
Condo in Magnificent Mile
4.33 out of 5 average rating, 9 reviews

30 E. Huron #2603 Private Residence

Diego HernanRating, 5 stars23 months ago
Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.
Guest favourite
Condo in Elk Grove Village
4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars1 month ago
I am incredibly particular with places I stay. This place was simple, very clean, had everything you would need to be comfortable. Bed was great! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️
Guest favourite
Condo in Evanston
4.91 out of 5 average rating, 124 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

NinaRating, 5 stars1 month ago
We had a great stay at Michelle’s “Heart of Evanston.” I loved the indoor garage parking option with easy in and out. If you have a large vehicle /SUV, maneuvering in and out of the spot may be challenging depending if the spot over is occupied. We have a mid-size SUV and had no issues. The room was easily accessed from the garage and we had no issues getting in. The place was clean and well organized. I loved that it smelled clean and also had a faint hint of bleach in the bathroom. It was a little warm in the bedrooms at night but we used the air conditioning to bring the temperature down. Town is very walkable and we enjoyed the local restaurants (Taco Diablo, Bat 17, Bennison’s bakery). We found the town to be very quiet - almost too quiet for what we expected but after our visit to Northwestern found out it was spring break for the students. Michelle was available for any questions and always replied promptly. We had a great stay and would stay again!
Guest favourite
Condo in Evanston
4.96 out of 5 average rating, 97 reviews

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

JohnRating, 5 stars1 month ago
We really enjoyed staying at Michelle's place. It was a perfect home away from home while visiting Northwestern University. The area had many cafes and restaurants. The place was spacious with three bedrooms and two bathrooms. The primary suite had a very firm mattress. But this did not bother us at all. The kitchen was well stocked with pots, pans, glasses, plates and utensils. There's a coffee maker and we were able to try some local coffees in the area. We enjoyed having family dinners on the bar style, raised table and stools. The view of the sunset from the balcony was amazing each night with purples, pinks and trees - fantastic views of Evanston. The place is great for watching movies with a long couch lounger, cozy seats and cup holders! The area is a perfect blend of city and nature with Lake Michigan nearby. We will definitely be back.
Condo in Downers Grove
4.87 out of 5 average rating, 54 reviews

Upscale, Smoke and Pet Free, Washer Dryer, Balcony

Lee AnnRating, 5 stars8 months ago
I have stayed at one of Briana’s places numerous times. They never disappoint. She is a great host and always responsive if I ever need anything. This condo is very clean quiet, and cozy. I highly recommend.

Quick stats about condo rentals in Rogers Park, Chicago

  • Total rentals

    40 properties

  • Nightly prices starting at

    $69 CAD before taxes and fees

  • Total number of reviews

    2.4K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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