Downtown Chicago vacation rentals
Book unique homes, vacation rentals, and more on Airbnb
Top-rated vacation rentals in Downtown Chicago
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Downtown Chicago vacation rentals
Home rentals in Downtown Chicago
Home in Oak Park
4.88 out of 5 average rating, 104 reviewsUrban Chic 3beds w/2bath + free parking & W/D
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.
Home in Glen Ellyn
4.92 out of 5 average rating, 127 reviewsHome in Glen Ellyn
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.
Home in Blue Island
4.81 out of 5 average rating, 182 reviewsWarm and comfortable inviting Suburban home !
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!!
Home in Des Plaines
4.73 out of 5 average rating, 89 reviewsHome for rent to traveling family and work.
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!!!!
Home in Homer Glen
5 out of 5 average rating, 3 reviews4 bedroom home rental in quiet neighborhood
Quiet neighborhood, spacious and comfortable home. The yard is inviting and a great entertaining space! Very kind hosts.
Home in Chicago
4.98 out of 5 average rating, 43 reviews4BD/4BTH - Entire Building+Garage - Wicker Park!
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!
Home in Prospect Heights
5 out of 5 average rating, 12 reviewsUpscale-5 Bed 4.5 Bath-3/4 Acre- 5400 sq ft
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.
Home in Addison
4.95 out of 5 average rating, 56 reviewsHome in Unincorporated Addison. RV & Pet Friendly
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
Condo in Chicago
4.9 out of 5 average rating, 218 reviewsA Stones Throw from U Chicago South Campus!
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.
Condo in Evergreen Park
4.8 out of 5 average rating, 109 reviewsEvergreen Park Condo with balcony and Jacuzzi tub
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!!
Condo in Chicago
4.95 out of 5 average rating, 117 reviewsEntire 3Bed/2Bath Condo Near McCormick & Metro
John is a nice and responsive host. The place is good and clean. It’s a walkable distance to Metro. Thank you John!
Condo in Chicago
4.9 out of 5 average rating, 101 reviewsConvenient & Spacious 3BR Condo w/Free Parking
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!
Condo in Chicago
4.92 out of 5 average rating, 131 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
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
Condo in Chicago
4.98 out of 5 average rating, 103 reviews💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!
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!
Condo in Chicago
4.98 out of 5 average rating, 241 reviewsNear Lake Michigan & Wrigley Field
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
Condo in Chicago
4.99 out of 5 average rating, 124 reviewsLuxurious River North 3BR/2BA- Free Onsite Parking
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
Rental unit in Evanston
4.82 out of 5 average rating, 164 reviewsMDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
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! 😊
Rental unit in Chicago
4.84 out of 5 average rating, 371 reviewsCozy Garden Unit In Edgewater
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.
Rental unit in Chicago
4.86 out of 5 average rating, 506 reviewsLogan Square Lookout
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.
Rental unit in Whiting
4.85 out of 5 average rating, 140 reviewsNEW! |Studio Apartment Whiting IN, United States#2
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.
Rental unit in Chicago
4.99 out of 5 average rating, 178 reviewsChicago Airbnb Newly Remodeled 2-Unit Apartment!
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.
Rental unit in Chicago
4.97 out of 5 average rating, 132 reviewsInviting 2 Bedroom Apartment in Roscoe Village
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!
Rental unit in Chicago
4.93 out of 5 average rating, 502 reviewsRestored Apartment in Historic Victorian Home
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!
Rental unit in Chicago
4.82 out of 5 average rating, 243 reviewsBERNARD CHATEAU - LOGAN SQUARE
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
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Evanston Vacation rentals
- Saugatuck Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Bend Vacation rentals
- South Side Vacation rentals
- Schaumburg Vacation rentals
- Chicago Vacation rentals
- Beachfront rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with a patio Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Condo rentals Downtown Chicago
- Monthly Rentals Downtown Chicago
- Hotel rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- House rentals Downtown Chicago
- Rentals with a washer and dryer Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with pools Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Kid-friendly rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a fire pit Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with a home theater Downtown Chicago
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Things to do United States
- Sports activities United States
- Food and drink United States
- Art and culture United States
- Wellness United States
- Sightseeing United States
- Entertainment United States
- Nature and outdoors United States
- Things to do Illinois
- Art and culture Illinois
- Food and drink Illinois
- Sightseeing Illinois
- Things to do Cook County
- Food and drink Cook County
- Sightseeing Cook County
- Art and culture Cook County
- Nature and outdoors Cook County
- Things to do Downtown Chicago
- Food and drink Downtown Chicago
- Art and culture Downtown Chicago
- Sightseeing Downtown Chicago
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes