
Holiday rentals with breakfast in Near North Side, Chicago
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Top-rated rentals with breakfast in Near North Side, Chicago
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Popular amenities for rentals with breakfast in Near North Side, Chicago
House rentals with breakfast

North Shore - Home Away From Home
Perfect place for our family gathering. Everyone had his own space and the kids had plenty of room to run around!

◆◆◆ Work, Play, Eat | 5B/3BA Near Everything ◆◆◆
FANTASTIC!! Great host! Awesome location! Clean house with everything needed available.. my kids loved the house, it felt like home away from home. Peaceful … Wish I could give more stars than 5!!!

Modern 3BR w/ Fenced Yard | LCP Collection
Dawn is definitely a Super Host her airbnb is exactly like the title, Classic Charm with Modern Flair, guests will not be disappointed , from the time you walk through the door until checkout, you'l feel you're in a 5-star hotel, but at home, it was roomy the beds(queen sized) in every room with hotel style linen amenities such as appliances which included washer and dryer and hair dryer, a sun room with games for children and family, TVs in every room except dining and fully equipped kitchen quality dining ware, I'm sure this summer will be booked full because there will be a great outdoor area to enjoy, bottom line I hope next time I visit my Chicago family, she will have availability, Dawn, Thank you !

Huge 2 Story Home/7miles from Downtown Chicago!
My family and I rented Kevin's place for my niece's wedding. we enjoyed ourselves and the accommodations. Kevin was super responsive and made us feel welcome. the neighborhood is isolated but peaceful.

Cozy 4-Bedroom House with Patio
Perfect place to stay for our visit to Chicago with friends! There was ample room in the BnB for all of us, including a spacious dining and living room. The kitchen was very well stocked including coffee, juice, eggs, and toast for us to make our own breakfast (a welcome surprise!). It was very walkable to transit, with a CTA Blue Line station nearby. Thatheu was very responsive and check in was straightforward. Also the later check-out time was very convenient as we were able to take the time for breakfast before heading out for the day. Thanks again for helping us to have a great trip!

Chic Cottage close to Metra large enclosed yard.
We had a wonderful experience staying at the Chic Cottage and would recommend it to any one looking for a comfortable home away from home place , available at a great price and good sub urban location with Super Markets and restaurants close by .

Laurna Dune
We had a wonderful stay at this property, it truly felt like a home away from home. The entire place was exceptionally clean, and the kitchen and dining area were spacious and easy to move around in. Both bedrooms were spotless, and the mattresses were incredibly comfortable. If you’re looking for a quiet, private place to stay, this is the perfect choice. I would definitely stay here again! 😊

The Ivy 1 minute walk to Wrigley Field
We rented this for a two night stay to attend a couple of Cubs games! You can’t beat the location!! Def go as early as you can before if it’s game day parking and getting through to the property was a beast because we arrived later than we planned.
Apartment rentals with breakfast

Comfy Solar & Green 2BR Near Hot Hyde Park!
Adam's place was very clean, comfortable, and well appointed. I appreciated the touches, the abundant parking in front, the proximity to the University of Chicago.

The "Nest", unconventionally modern yet vintage.
I enjoyed the apartment, it was very nice. It lived up to the pictures and description on the listing.

Magical Treehouse Located in HEART of Old Town!
We had an absolutely wonderful and positive experience staying at this place! Our host was extremely responsive and friendly which made our experience even better! It was a great location and walking distance from a lot of great restaurants and bars. Perfect place to host a big group looking for a fun time.

Charming Unique 2 Bdrm Apartment in Victorian Home
Carol’s place was very comfortable for our family of 4! Amenities were all as listed and everything was clean and inviting. We hope to stay here again the next time we visit family in Blue Island!

Easy, Cool, safe place to stay.
It was a nice place. Had everything needed. The locality is really good. Quiet, peaceful and nice people.

Ashland Ice Cream House
The house was comfortable and spacious

The Garden on Wayne
One of the best Airbnb's we have stayed in. The location is great with excellent bars and restaurants nearby, but in a quiet street. The accommodation is as advertised, but also includes everything you need for cooking and generally relaxing. I wouldn't hesitate to recommend this place and if we come to Chicago again I would definitely try and stay here

2Bed 2Bath 15min to Wrigley with Parking& Balcony
Incredible place! Location was perfect with easy access to public transportation and great food. Host recommendations were immaculate and responsive+kind. Plenty of extra blankets pillows and towels, the jacuzzi was really nice, and the bathrooms were spotless. Very easy check in and check out process. Had almost no problems with any amenities. The smart thermostat did keep setting itself to 75 degrees or more during the night even after we set it low before sleep. Quite uncomfortable to sleep through. And the listing stated 5 beds with 2 air mattresses but there was only 1 air mattress, making a total of 4 beds. Not a huge problem but good to know for anyone who needs all 5, we didn’t. Water pressure in one shower was not great and the other drained slowly. Also some areas were a little dusty but again it was fine. Overall, this was a really really great experience and apartment. Couldn’t have asked for a better place to stay during our trip!
Bed and breakfast rentals with breakfast

Bright Room with a Garden View
You get exactly what you look for. The location is awesome and I found parking immediately. Great place

Urban Oasis Pilsen - guest room in townhouse
I recently had the pleasure of staying at Christiane's & Patrick’s beautiful home, and I can't recommend it highly enough! From the moment I arrived, I felt welcomed and at home. The space is impeccably clean, beautifully decorated, and equipped with everything I needed for a comfortable stay. Both were outstanding host—responsive, friendly, and full of great local recommendations. They went above and beyond to ensure my stay was perfect, checking in to make sure I had everything I needed.

Cloudgate Room, minutes to O'Hare in Safest Area
Very cozy place in a calm tucked away neighborhood. Would definitely stay again!

Chicago River Room near USMLE
Mary's place was a great location for our short trip to Chicago! It was a short Uber drive from the airport, and a short drive to the All-State Arena. We did arrive late at night due to flight delays and opted for an Uber versus the train. I am glad we did cause it seems like the train station is under construction for the side we needed and would have been a bit more of a walk departing from the other side, but definitely not a dealbreaker or anything. The house is a short walk from this breakfast place that we actually went to twice during our short stay, with other options nearby. Overall, the house felt cozy and clean, but we did struggle with getting in the bathroom first thing in the morning with the other guests in the house during our stay. Mary was very responsive and a great host to us during our stay. The bed was comfortable as well and the room had amble space for a large suitcase, a carry-on, and two large bags with space to spare for two people.

King Bed with Jet Tub
Nidhi’s place was exactly as described. I can’t say enough good things about it. The bed was very comfortable. The Jacuzzi and mood lighting was fun. The dorm size fridge and microwave wow you don’t normally see that in a motel anymore. Everything was clean and the water pressure was very good. Plenty of hot water.. I was shocked that every morning a full complete breakfast was in the lobby for free not to mention 24 hour coffee! We were there on a business trip and across the street were excellent restaurants, including an upscale bar with delicious meals, a sushi house, Chinese restaurant and a diner. You could also get your nails done and book a massage right across the street. I enjoyed taking the train into Chicago. It was very simple to buy your ticket on the spot not far from the motel at the station. The neighborhoods surrounding her place were beautiful. I did a lot of walking and there were sidewalks everywhere making it safe. She and the check-in managers we’re friendly.

Lovely UofC Prof mansion great on campus location
I always enjoy stays at the Hamlin House and this was no exception! The Blue Room is lovely, - spacious with gorgeous windows and a spa-like bathroom. Wish I could have stayed longer!

Classy and Cozy home in Evanston
We've stayed in many dozens of Airbnb's -- most that we've liked a lot -- and our hosts here, Joaquin and Patricia, were top of the list. They are absolutely delightful company, and provided a beautiful home and delicious breakfast. Moreover, Patricia is an accomplished artist whose paintings adorn the walls, and Joaquin is a collector of interesting books (amongst other things) that populate bookshelves throughout the house. Our bedroom and bathroom were very comfortable and spacious. Pillows and bed were excellent (we're sensitive to both so these are items we especially notice when we travel), as was the shower. The house is located on a cul-de-sac in a cute neighborhood. It's a quick uber ride to the lake or into Skokie. In summary, we highly recommend this airbnb.

(BR#1) Welcoming, warm & comfortable, 3 guests
Great communication and a comfortable stay!
Quick stats about holiday rentals with breakfast included in Near North Side, Chicago
Total rentals
30 properties
Nightly prices starting at
₹865 before taxes and fees
Total number of reviews
570 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club