Apartment holiday rentals in Downtown Chicago

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Popular amenities for Downtown Chicago apartment rentals

Weekly apartment rentals

Superhost
Apartment in Chicago
4.85 out of 5 average rating, 34 reviews

City View 3BR Condo/Garage Parki

JeffreyRating, 5 stars1 month ago
Shivani and Riya’s place was a great spot for a weekend with friends to catch up and watch March Madness. There was plenty of space for our group of 6 and the place was exactly as described. The location also can’t be beat. There were tons of great restaurant and bar options within walking distance. I would definitely stay at this location again!
Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 51 reviews

NEW! Spacious Modern 5 BD Condo

MichelleRating, 5 stars2 weeks 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
Apartment in Chicago
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.
Superhost
Apartment in Chicago
4.79 out of 5 average rating, 29 reviews

Spacious condo with open floor plan and fireplace

TatianaRating, 5 stars3 months ago
This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.
Top guest favourite
Apartment in Chicago
4.92 out of 5 average rating, 259 reviews

Modern/Spacious 2BR/2BA West Town

JaslynRating, 5 stars1 month ago
We had a great stay! The pictures did not do the space justice, we loved it! And Charissa was so friendly and responsive, it really made our trip so easy
Superhost
Apartment in Chicago
4.8 out of 5 average rating, 249 reviews

Logan Square Beauty with 2 Bedrooms W/parking

SarahRating, 5 stars6 days 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
Apartment in Chicago
4.92 out of 5 average rating, 153 reviews

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

AbiolaRating, 5 stars2 weeks ago
This was an amazing stay!! Eugene was so so helpful and he responds so quickly. Great location, peaceful, safe. 10/10 would absolutely recommend.
Superhost
Apartment in Chicago
4.81 out of 5 average rating, 135 reviews

Marvelous Condo w/ Pri Prkng Cls to Transit &Beach

NicholasRating, 5 stars4 days ago
Very quick to respond to questions and great detailed instructions. The place was clean and comfortable! Awesome!

Pet-friendly apartment rentals

Guest favourite
Apartment in Chicago
4.85 out of 5 average rating, 131 reviews

816 PLZN Luxury Apt | Rooftop | Garage Parking

SabrinaRating, 5 stars2 weeks ago
such a great lovely place to stay thank you for the great hospitality!
Superhost
Apartment
4.7 out of 5 average rating, 223 reviews

Studio flat in the heart of Chicago's Gold Coast

HeatherRating, 5 stars2 weeks ago
This is our second stay here. the location can't be beat and we will continue to stay here when we are in chicago. I will note that it is VERY loud. Depending on who you have above you can make it even louder. the pipes for the heat are also extremely loud. This doesn't bother us so much as we go in expecting it. This is also not the fault of the host at all and this airbnb and host are both still great!
Guest favourite
Apartment in Chicago
4.93 out of 5 average rating, 114 reviews

The Fox Den

JamesRating, 5 stars2 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
Apartment in Chicago
4.89 out of 5 average rating, 112 reviews

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

JasonRating, 5 stars2 weeks ago
Wonderful, everything was clean and lots of fun stuff nearby I recommend anyone book here it’s a great stay
Superhost
Apartment in Chicago
4.85 out of 5 average rating, 129 reviews

Downtown Mich Ave #7| Park View Penthouse +gym

SachinRating, 5 stars1 week ago
Best place to stay in Chicago with family and friends: centrally located in downtown Chicago, with public transport and bars & restaurants within walking distance.
Guest favourite
Apartment in Chicago
4.92 out of 5 average rating, 230 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

MartinRating, 5 stars2 weeks ago
This place was fantastic. Exactly what I thought it was going to be from the description and pictures. Kaye was super responsive and helpful when we needed info or to borrow something. She is a super host indeed. Will definitely be back!
Guest favourite
Apartment in Chicago
4.91 out of 5 average rating, 339 reviews

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

JeffRating, 5 stars1 week ago
This was our second stay at Susan’s. We love the location for visiting family in Logan Square. Convenient to bus on Diversey to go to Wrigley Field, and easy to park on Western to take Blue Line into Loop. Dining room table seats 6, kitchen is perfect for preparing brunch & dinner for all of us (6). Unit is very clean, garage is a great perk. Susan is very responsive and helpful. Will likely stay here again (if available) for future visits to Chicago.
Top guest favourite
Apartment in Chicago
4.98 out of 5 average rating, 249 reviews

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

KristinRating, 5 stars2 weeks 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!

Apartment rentals with a pool

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

Upscale, Washer Dryer, Smoke Free, Pet Free,

NormaRating, 5 stars3 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
Apartment in Evanston
4.96 out of 5 average rating, 93 reviews

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

SeanRating, 5 stars1 week ago
Really great place with lots to do nearby!
Guest favourite
Apartment in Evanston
4.96 out of 5 average rating, 104 reviews

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

JasonRating, 5 stars4 days 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!
Apartment in Chicago
4.2 out of 5 average rating, 5 reviews

voco: Balcony & City View

GavynRating, 5 stars1 month ago
Overall very nice place for the price. Only disappointment was I got to the location listed on the air bnb listing and the actual location was 3 to 4 blocks away which I was a bit upset with. It is closer to the Chicago station on the redline than it is to the river where the listing states. Host was very responsive and allowed me to check out late to avoid waiting around at the airport for a long time.
Apartment in Chicago
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
Apartment 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
Apartment in Evanston
4.91 out of 5 average rating, 124 reviews

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

NinaRating, 5 stars4 weeks 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
Apartment in Evanston
4.96 out of 5 average rating, 97 reviews

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

JohnRating, 5 stars4 weeks 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.

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