Downtown Chicago vacation rentals

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Popular amenities for Downtown Chicago vacation rentals

Home rentals in Downtown Chicago

Guest favorite

Home in Oak Park

4.88 out of 5 average rating, 104 reviews

Urban Chic 3beds w/2bath + free parking & W/D

TaylorRating, 5 stars6 days ago
We loved staying at Tiffany's home in Oak Park. Such a lovely area and home. We were grateful that there was a spot to park behind the house instead of on the street. Check in was easy. The big blue couch in the living room is so cumphy. A great place to kick back and watch a movie after a day of walking. We appreciated the noise machine in the bedroom. That definitely came in handy. We do have kids but did not bring them for this trip. Tiffany's house has a room with a play area and a bunk bed for the kids. She also has a pack and play and a high chair. There was also a nice selection of coffee for the Keurig. We would stay here again. Great Neighborhood, felt safe.
Guest favorite

Home in Glen Ellyn

4.92 out of 5 average rating, 127 reviews

Home in Glen Ellyn

ChristianRating, 5 stars5 days ago
This was the second time our group stayed at Mir's house--we appreciate the size, how well taken care of the house is, and how easy check in and check out are. It's a great location.
Guest favorite

Home in Blue Island

4.81 out of 5 average rating, 182 reviews

Warm and comfortable inviting Suburban home !

SaraRating, 5 stars2 weeks ago
Rich's place was the perfect location for us. We needed to get to the city for the Chicago Marathon, but didn't want to stay IN the city. Check in and check out were easy. The place was clean, spacious, and comfortable. Thank you!!
Guest favorite

Home in Des Plaines

4.73 out of 5 average rating, 89 reviews

Home for rent to traveling family and work.

SavanahRating, 5 stars2 months ago
We had an amazing time at Raul’s place!! It is a beautiful home, in a quiet and friendly neighborhood! The back patio is wonderful to sit and relax, the living room areas are perfect for you and your guests to relax, and it was pristine and welcoming!!!! Raul was an amazing host, and was very responsive! We will definitely be back!!!! Thank you Raul!!!!
Superhost

Home in Homer Glen

5 out of 5 average rating, 3 reviews

4 bedroom home rental in quiet neighborhood

LoriRating, 5 stars65 months ago
Quiet neighborhood, spacious and comfortable home. The yard is inviting and a great entertaining space! Very kind hosts.
Guest favorite

Home in Chicago

4.98 out of 5 average rating, 43 reviews

4BD/4BTH - Entire Building+Garage - Wicker Park!

BlaneRating, 5 stars2 weeks ago
The place and location are fantastic! Our family attended a wedding in downtown Chicago and it was perfect for us! Very charming home and neighborhood! We would definitely stay there again and highly recommended!
Guest favorite

Home in Prospect Heights

5 out of 5 average rating, 12 reviews

Upscale-5 Bed 4.5 Bath-3/4 Acre- 5400 sq ft

YousufRating, 5 stars2 weeks ago
Ben was very responsive throughout our stay, place was clean and big enough for us to stay comfortably. Location was quite centric, everything within 30mins. Would definitely come back if I am in Illinois again.
Guest favorite

Home in Addison

4.95 out of 5 average rating, 56 reviews

Home in Unincorporated Addison. RV & Pet Friendly

WhytneiRating, 5 stars2 weeks ago
it’s was a great stay, very roomy for a family of 6. The neighborhood was very good and quiet and peaceful. I’ve enjoyed it the whole Xavier. He was very nice and always very responsive quickly and I would love to stay again.

Condo rentals in Downtown Chicago

Guest favorite

Condo in Chicago

4.9 out of 5 average rating, 218 reviews

A Stones Throw from U Chicago South Campus!

MonicaRating, 5 stars4 days ago
The place is literally next to the University. Very clean well stocked and super Comfortable. Luke made sure to let me know there might be an internet outage due to maintenance which didn’t even affect us. The beds were super Comfortable. What I would say is if you have never slept in a city type apt you might have to get use to the upstairs walking and noise but nothing crazy. I will definitely recommend this place and I will definitely stay here again when coming back.
Guest favorite

Condo in Evergreen Park

4.8 out of 5 average rating, 109 reviews

Evergreen Park Condo with balcony and Jacuzzi tub

McKenzieRating, 5 stars1 month ago
Had a great stay!!! Felt right at home and enjoyed having a nice quiet place to stay after a long day in the city. The condo is so cute and was exactly what we were looking for!!
Guest favorite

Condo in Chicago

4.95 out of 5 average rating, 117 reviews

Entire 3Bed/2Bath Condo Near McCormick & Metro

Natalie ChanRating, 5 stars1 week ago
John is a nice and responsive host. The place is good and clean. It’s a walkable distance to Metro. Thank you John!
Guest favorite

Condo in Chicago

4.9 out of 5 average rating, 101 reviews

Convenient & Spacious 3BR Condo w/Free Parking

EricRating, 5 stars5 days ago
Outstanding place! The property was exceptionally clean, comfortable, and exactly as described. We had no issues at all during our stay, and the host’s communication was excellent—quick, clear, and very helpful. The space felt welcoming, and everything we needed was provided. We’d definitely stay here again and highly recommend it to others looking for a worry-free experience. Thank you for a fantastic stay!
Guest favorite

Condo in Chicago

4.92 out of 5 average rating, 131 reviews

Modern designed 2bed/2bath | Heart of Bronzeville!

UniqueRating, 5 stars1 week ago
The host was amazing, would book with him again. The only part was the kido upstairs was loud especially in the mornings but that was out of his control and kids will be kids. He also responded to any questions within 5 minutes everytime and I appreciate that. So thank you
Guest favorite

Condo in Chicago

4.98 out of 5 average rating, 103 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

KateRating, 5 stars1 week ago
We loved staying here for my birthday trip while we searched for an apartment in Chicago. Everything was spotlessly clean and well maintained, amenities were excellent, and I slept better than I ever have away from home! I typically have a lot of travel anxiety and I never felt concerned or uneasy here. The value is excellent and the neighborhood is wonderful. We would highly recommend this spot to any family and friends visiting us in the future!
Guest favorite

Condo in Chicago

4.98 out of 5 average rating, 241 reviews

Near Lake Michigan & Wrigley Field

KelseyRating, 5 stars2 weeks ago
Brian’s place was awesome and he made it such an easy process we hardly had to think about anything and felt right at home. Couldn’t ask for a better location, there was a lot to do within walking distance and short easy drive downtown, his place was very clean and comfortable. With luxurious bathroom experience, would definitely recommend 10 out of 10
Guest favorite

Condo in Chicago

4.99 out of 5 average rating, 124 reviews

Luxurious River North 3BR/2BA- Free Onsite Parking

LindsayRating, 5 stars1 week ago
We had a great time and really enjoyed our stay! Plenty of space, beautiful and clean, nice touches throughout the unit, comfortable beds, a gated parking space right there, convenient to so many things… the list goes on and on. Our hosts even dropped some fantastic donuts off on our last morning. We highly recommend this airbnb!

Apartment rentals in Downtown Chicago

Superhost

Rental unit in Evanston

4.82 out of 5 average rating, 164 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

RobertRating, 5 stars3 weeks ago
We have been multiple stay guests, and wouldn't consider staying anywhere else but here, when whenever traveling to the area! We are already booked in both units this coming week as well! 😊
Guest favorite

Rental unit in Chicago

4.84 out of 5 average rating, 371 reviews

Cozy Garden Unit In Edgewater

JoanRating, 5 stars1 week ago
The bed is super comfy and the living area is large and very tidy. The linens are well stocked. The TV has Netflix and maybe other services but we just used Netflix. Thomas is very considerate and reached out to us prior to getting there to make sure we had all the information we needed for check-in. The location is fabulous. A tree-lined peaceful street, quiet and safe. Thomas offers garage parking but we did not have a car. Walking distance to Whole Foods; Cozy Corner for breakfast; Sauce and Bread for pastries and lunch; Alexander’s for breakfast; Ann Sather for breakfast; Metropolis for delicious coffee. Thomas has a hot water kettle and a drip coffee maker and a Keurig. Highly recommend this Airbnb.
Superhost

Rental unit in Chicago

4.86 out of 5 average rating, 506 reviews

Logan Square Lookout

AllisonRating, 5 stars3 weeks ago
We really enjoyed our stay here. the location is great and since we drove to Chicago we needed a place with parking. Being able to park on the street was perfect. The neighborhood was great and Patrick responded to all my questions. We would definitely stay here again.
Superhost

Rental unit in Whiting

4.85 out of 5 average rating, 140 reviews

NEW! |Studio Apartment Whiting IN, United States#2

ChelseaRating, 5 stars2 weeks ago
A nice place to stay for a night or two. It was a quick drive to Chicago for us. Marlen was a very responsive host and communicated well throughout our entire stay.
Guest favorite

Rental unit in Chicago

4.99 out of 5 average rating, 178 reviews

Chicago Airbnb Newly Remodeled 2-Unit Apartment!

MichelleRating, 5 stars1 week ago
I loved staying at this house. Everything was clean and most importantly, the home is located within15-20 minutes away from Downtown Chicago. My only hiccup was the bed… the bed was very uncomfortable and there were no televisions inside the room.
Guest favorite

Rental unit in Chicago

4.97 out of 5 average rating, 132 reviews

Inviting 2 Bedroom Apartment in Roscoe Village

AlexaRating, 5 stars3 weeks ago
Laura’s place was perfect! Very walkable to shops and restaurants in Roscoe Village. Quiet, safe neighborhood. Easy check in with key pads. Two bikes were available on the back patio for use with locks. She provided extras such as a few Kuerig coffee pods, board games, a brita water filter filled on arrival, and several ice trays already frozen. Very clean, comfortable beds. We would definitely stay here again!
Guest favorite

Rental unit in Chicago

4.93 out of 5 average rating, 502 reviews

Restored Apartment in Historic Victorian Home

CharlieRating, 5 stars1 month ago
Lynn’s apartment is an idyllic place to base yourself to explore Chicago. The space feels like home and is really beautifully decorated and her locals recommendations were excellent. The stand out feature is its location in Old Town - I’m not sure we would have explored this neighbourhood to the extent we did had we not stayed here and it really was the highlight of our trip. Thank you!
Guest favorite

Rental unit in Chicago

4.82 out of 5 average rating, 243 reviews

BERNARD CHATEAU - LOGAN SQUARE

MeghannRating, 5 stars1 week ago
Will 100% book again!! This space is exactly like the photos!! Absolutely gem to find this much space in the city. The location was perfect with easy access to blue line and being walkable to the dreamy Logan Square activities!! We felt safe walking around! Mike and Clemencia were extremely quick with responding and the check in and out directions were clear and easy to do. Do yourself a favor and stay here!!!

Frequently Asked Questions

  • How is the weather in Downtown Chicago?

    Downtown Chicago experiences a diverse climate. Summers can be hot, typically reaching 85°F (29°C), while winter temperatures can drop to around 20°F (-6°C), often accompanied by snow. The transitional seasons, spring and fall, offer more moderate weather, making them pleasant times to visit.

  • What are some of the best things to do in Downtown Chicago?

    There's no shortage of activities in Downtown Chicago. Explore the Art Institute of Chicago, walk alongside the Chicago River, or enjoy a stroll in Millennium Park. You can also marvel at the city's skyline from the Willis Tower's Skydeck or take a boat cruise on Lake Michigan.

  • What is the best time of year to visit Downtown Chicago?

    The summer months, from June to August, are a great time to explore Downtown Chicago as the city comes alive with a range of cultural events including Lollapalooza, the Chicago Air and Water Show, and the Jazz Festival. However, the city also offers distinctive charm during the winter season, with events like the Magnificent Mile Lights Festival and the Winter WonderFest.

  • What are the best places to stay in Downtown Chicago?

    Guests enjoy staying in several areas in Downtown Chicago. The Loop, Chicago's central business district, is known for its bustling atmosphere and close proximity to many attractions. River North, with its art galleries and fashion outlets, is also popular. Streeterville, near Navy Pier and Magnificent Mile, is another preferred location.

  • What are the best places to visit in Downtown Chicago?

    There are many popular places to visit in Downtown Chicago. These include the Navy Pier, with its iconic Ferris wheel, the Art Institute of Chicago, known for its impressive collection, and the historic Chicago Theatre. Don't miss a walk down the Magnificent Mile for shopping and dining.

  • What are some hiking trails in Downtown Chicago?

    While Downtown Chicago is primarily urban, there are lovely trails to explore. The 18-mile (29 km) Lakefront Trail along Lake Michigan is a favorite among locals and visitors. The Chicago Riverwalk also provides a scenic urban hike through the heart of the city.

  • What are some family activities to do in Downtown Chicago?

    Families in Downtown Chicago can explore a multitude of engaging activities. Visit the Shedd Aquarium or the Field Museum for an educational outing, enjoy outdoor fun at Maggie Daley Park, or discover the wonders of space at the Adler Planetarium.

  • What are some of the best day trip ideas in Downtown Chicago?

    For day trips, consider exploring the natural beauty of the Chicago Botanic Garden or the historical architecture in Oak Park, both within a short drive from Downtown. Alternatively, the Indiana Dunes National Park, 50 miles (80 km) away, offers an escape to nature.

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Downtown Chicago