
Holiday rentals with a balcony in North Side
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Apartment rentals with a balcony
The Craftsman Gallery at OHC - No Cleaning Fee!
My family came for a long weekend during spring break and had a great time! CVS and local market across the street. Walkable to lots of good coffee shops and restaurants. A block or so away from the Blue line which made going into downtown super easy. The place was clean, cozy, and we all loved the artwork!

Perfect Lincoln Park Retreat - Walk to Depaul!
Catherine is a very responsive host. The apartment was exactly as described - clean, great location. It sleeps four people comfortably. There is a futon couch in the living room but I think only a small child would be comfortable sleeping on it. With that being said, I would definitely recommend Catherine’s apartment and would rent it again when in Chicago.

2 Cozy Bedrooms In a Hidden Wicker Park Gem!
This place was spectacular. Minutes away from the blue line and close to other bus stops. Very cute and quiet space in a beautiful neighborhood. Tea bags and enough plates/cups for our party of 6. We could all fit on the couch/living room which was awesome! Cannot recommend this place enough !! Would definitely stay again :)

Cozy Lincoln Park Studio - Steps to Zoo!
Great location and perfect for a couple. Comfortable bed and just the right amount of amenities. Maureen was extremely responsive and friendly. Would not hesitate to stay here again!

Spacious & Clean Ukrainian Village 2 Bedroom!
We have stayed here before, and certainly will again. It is such a comfortable place to stay - clean, spacious, with a well-stocked kitchen (including the much-appreciated coffee for the coffeemaker!) The Ukrainian Village neighborhood is wonderful and peaceful, but close enough to restaurants and a supermarket. When we were first considering this Airbnb, the comment that helped the most was someone saying "don't be put off by it being a basement-level apartment". That is so true. There is plenty of light, there is heating in the floors in winter, and it is so carefully designed and constructed that it has none of the feel of a "basement".

Artsy Chicago Abode: Steps to Shops & Restaurants
Had a nice stay. Did the trick as a place to sleep while exploring the city. Good location

3 Bed 3 Bath Lakefront Oasis, Parking Included
I would stay again
The Woodsman's Gallery at OHC - No Cleaning Fee!
Our stay was great! Matthew is an awesome host - responsive, helpful, and friendly. The place is spacious, clean, and funky, as well as easily walkable to nearby food options and the subway. Would definitely stay here again, and keen to try out one of the other OHC properties too.
Holiday House Rentals with a balcony

The Roscoe House near Wrigley Field
We came with a group 4 adults and 4 kids to see a game at wrigley and explore the city. the house and location were both perfect for what we needed and a great 'home base' for a long weekend of activities. Would recommend highly if you're visiting Wrigleyville or Chicago.

6 Bedrooms In Beautiful Sheridan Park!
Had a great stay over St. Patrick’s day weekend. The apartments are in a very walkable area with great access to public transportation. Fenton was also very quick to communicate and gave clear instructions. 10/10 would recommend to anyone.

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl
The location alone makes this home worth booking. Add that there’s ample room for family/friends and it’s a gem in the middle of a great Chicago neighborhood. We were a group of six and loved every minute.

Newly Updated Vintage 6 Bedroom Single Family Home
Shabbir's place was perfect for our family of 10 during the holidays. We spent Christmas and New Year here, and the house had everything we needed for a comfortable and memorable family reunion. The private parking was very convenient, and the house was fully equipped with everything we needed. Its location was ideal—just 10-15 minutes from all the major attractions in Chicago and about 30 minutes from the airport. We also enjoyed exploring the nearby local restaurants and an Italian bakery with great takeout options. The host was very responsive and made sure everything went smoothly during our stay. We would stay here again and highly recommend it!
Southwestern Escape in Logan Square, Sleeps 12
My friends and I celebrated the new year in Chicago and were so grateful to find this place! Logan Square is a great neighborhood with plenty of coffee shops, bars, and restaurants. The apartment was easy to access and very clean. It was particularly clean for a place that people use for celebrations and parties! I really appreciated that. Bathrooms were roomy, great fixtures, and nice decor. Thank you for a wonderful stay! I’d happily book it again.

Sunny Character-Filled Apartment in Trendy Ukrainian Village
Hosts are super kind & very responsive — area feels very welcoming and safe — Space was beautifully decorated & had everything we needed for our stay. I would definitely recommend staying here if you’re visiting Chicago!!

Spacious Retreat Near Convention Centers
My colleagues and i stayed here for a tattoo convention. We all enjoyed the place, found the rooms to be accommodating especially with a group as big as ours (9 people.) The neighborhood was quiet, but still close to everything you need. We had no issues our entire trip. Definitely a more hands-off host, which we appreciated! 10/10 recommend for anyone needing to stay close to the chicago area.

The Grand Kimball Lodge, Logan Square, Sleeps 14
We loved this place. Stayed here for a bachelor party trip, and the Airbnb was one of the many highlights of the trip. Bob was cool, super friendly, and helpful. The location is about a 15-minute walk + 15-min L-Train ride from downtown. I'd highly recommend checking out the neighborhood bar Best Intentions, which is close to the Airbnb. We also really enjoyed the sauna located in the courtyard of the Airbnb.
Holiday condos with a balcony

Newly Designed 3bd In Heart of Ukrainian Village
I appreciate how host was responsive to my messages. I was not fully aware of the way to put the parking sticker in my car window and incurred a $75 ticket for posting it on the interior left side and not right side. This was not any fault of the host, just very disappointing that the local security was not more mindful as the sticker was there, just wrong side and I was from out of state. The kitchen was nice, however if you plan to cook much, bring a 9x13 casserole dish and some pot holders.

Loft-Like Wicker Park Condo Steps from the Cta!
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.

3 Bedroom Vintage Hideaway In Little Italy/uic
Very quiet Peaceful and plenty of spaces for parking Host was great the response was great! I would definitely recommend this place!

Logan Square Beauty with 2 Bedrooms W/parking
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.

Can't Beat This 2min Walk to Wrigley!
My friend and I really enjoyed this spot. I loved everything about it. It was perfect for what we wanted to do in the city for 4 days. Amazing spot for Cubs games. You can even see and hear the crowd from the front door. How exciting! And the Cubs decor warmed my heart. It had everything we needed, and wanted. I appreciated Kimberly’s attentiveness and responsiveness. Thankfully we didn’t run into any issues. Highly recommend this place and wouldn’t hesitate to come back again in the future.

Sleek Wrigleyville/Boystown Condo with Rooftop Skyline Views
Nathan was a pleasure! He was very responsive and prompt answering my questions and very helpful assisting with parking. Having a dedicated parking space close by was a big plus. We had privacy and felt right at home. We had a great stay.

Duplex Near the Beach! 3 Bedrooms In Andersonville
This place was very nice. The beds and pillows were very comfortable. The kids enjoyed playing with the pool table. There was enough pots & pans, plates, cups, bowls & silverware for the 6 of us. The pans were a little small (had to cut bacon strips in half to cook in pan & cook 3 lbs of ground beef split in 2 portions). The fridge was big, clean & loved having two different ice sizes. The major downside was parking. We rented a car because we wanted to explore Chicago so the street parking around the neighborhood was rough. There ended up being a fire in one of the near by buildings & we had to wait for the fire trucks to move (blocked in). Another time we had to back out & drive the wrong way to get out. The train station was under construction but I’m it could’ve been an option if we weren’t traveling with young kids & at night. Not an expensive cost to take an uber to Wrigley Field for the 6 of us. We had a great time! Alex was really responsive & helpful. Would say again.

Spacious & Elegant Old Town Duplex
Was there for work and shared it with a few other coworkers. All in all it’s a great place, spacious and comfortable. A few things do not work (fireplace, fridge water dispenser, 2 burners in the stove) but we still had a great time and work/ relaxed while there. Location is great and easy to get to from train at any time. The building is a bit noisy but we did not care.
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Six Flags Great America
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Flossmoor Golf Club
- Museum of Science and Industry
- Wicker Park
- Willis Tower
- Lincoln Park
- Chicago History Museum
- Skokie Country Club
- Illinois Beach State Park
- Washington Park Zoo
- Promontory Point
- Things to do North Side
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- Food and drink North Side
- Wellness North Side
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