Far North Side Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Far North Side

Elegant 3 Bedroom and 1 Bath Apartment

9.0 out of 10, Wonderful, (10)
"Very nice place - can easily fit quite a few people! Host was very accommodating, place was clean and comfortable. My friends and I had a great time! "
Elegant 3 Bedroom and 1 Bath Apartment

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (175)
"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."
Walking distance to restaurants, shops and Lake Michigan,

Urban Chicago Vacation Rental Condo Near Beach!

9.2 out of 10, Wonderful, (17)
"This apartment was so cute, quiet and a great stay for my family and I. The host was able to accommodate extra blankets and towels for us during our stay. As well with it being a pet friendly property our dog enjoyed his stay and a little bit of the city life. Dinner is walkable as well as access to the main transit system. This is definitely a good spot for a girls trip or even a single that wanted to different kind of stay in Chicago!"
Urban Chicago Vacation Rental Condo Near Beach!

Your Chicago Home Base – 4BR, 2BA, Sleeps 13, Ideal for Families & Groups!

Your Chicago Home Base – 4BR, 2BA, Sleeps 13, Ideal for Families & Groups!

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (731)
"Thank you for accommodating us in your property it was devine!! And huge thank you to the front desk ladies! You rock!"
The price is HK$851
HK$1,227 total
includes taxes & fees
23 Apr - 24 Apr
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (477)
"Good place"
The price is HK$1,042
HK$1,223 total
includes taxes & fees
23 Apr - 24 Apr
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (273)
"Very clean l, quiet and well thought out. Had everything we needed and the bed was super comfortable! Great having a 12 cup coffee pot! Parking was close and although not a lot of close options to restaurants or shopping, there were many more options within a 15-20 min walk. Would definitely stay here again!"
The price is HK$1,059
HK$1,243 total
includes taxes & fees
24 Apr - 25 Apr
Sonder Market Hall

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (160)
"We loved the proximity to Union Station as well as Willis Tower and St. Patrick's Church. Casual dining options were very close and convenient. The apt was very clean. The view was of an alley which as expected had trash around dumpsters. It was brightly lit at night. A number of panhandlers in the area, which wasn't a complete surprise considering it's a city. The loveseat was the worst part... extremely uncomfortable and worn out. That being said, we would stay there again, because the check...
The price is HK$991
HK$1,164 total
includes taxes & fees
24 Apr - 25 Apr
Sonder The Burnham Apartments

Sonder Onterie

3.5 star property
8.4 out of 10, Very good, (13)
"The stove, washer/drier, plates, silverwear, beds, everything was obviously cleaned throughly. Was very impressed with how spotless everything was"
The price is HK$1,199
HK$1,408 total
includes taxes & fees
23 Apr - 24 Apr
Sonder Onterie

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (304)
"Only thing was no communication on the pool location and the arcade games so I just didn't go and how to work the stove other that it was a beautiful experience. I think you should let people smoke on the balcony. I mean it is a expensive location and marijuana is legal a recreational use think about it. "
The price is HK$1,489
HK$1,921 total
includes taxes & fees
24 Apr - 25 Apr
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (392)
"it was as it advertising. clean, tourist friendly "
Kasa Magnificent Mile Chicago

Sonder Jewelers Row

3.5 star property
8.4 out of 10, Very good, (148)
"This was the perfect stay for us this past weekend "
The price is HK$1,227
HK$1,440 total
includes taxes & fees
12 May - 13 May
Sonder Jewelers Row

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (275)
"We had a great time"
Kasa South Loop Chicago

The Neighborhood Hotel-Little Italy

3.5 star property
9.8 out of 10, Exceptional, (151)
"Very clean property, very convenient area offering restaurants, bars, groceries within walkin distance. Staff/owners very helpful. Answered all our questions promptly. Overall very pleased with our stay and I highly recommend this hotel when visiting Chicago."
The Neighborhood Hotel-Little Italy

Sonder The Plymouth

3.5 star property
8.4 out of 10, Very good, (97)
"The apartment was perfect. Location made everything walkable. Super clean. Bright rooms. Bed was super comfy. I can’t say enough good things about this place. I loved it and would stay here again on my next trip to Chicago "
The price is HK$1,053
HK$1,236 total
includes taxes & fees
12 May - 13 May
Sonder The Plymouth

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (33)
"Very very cozy and clean! All messages and questions were answered promptly, and checking in and out was smooth! getting into the building was easy, everything was perfect. "
The price is HK$873
HK$1,024 total
includes taxes & fees
11 May - 12 May
Sonder The Opal

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (136)
"Wow was the word we all exclaimed when we walked in the door. Beautiful corner rooms, light and airy, wonderful experience. "
The price is HK$1,518
HK$1,783 total
includes taxes & fees
23 Apr - 24 Apr
Kasa River North Chicago

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (47)
"I was in the mood to walk, so I put on my sneakers and did just that. The property is a little off the beaten track, and I was not that impressed with Greek Town, but I would stay again because the property itself was quite nice. "
The price is HK$1,159
HK$1,361 total
includes taxes & fees
27 Apr - 28 Apr
Sonder Greektown

Wrigleyville Suites

2.0 star property
9.4 out of 10, Exceptional, (3)
"Very good place at a very good price! Communication is the only need for improvement in my opinion. "
The price is HK$1,118
HK$1,700 total
includes taxes & fees
23 Apr - 24 Apr
Wrigleyville Suites

HUGE! 3bdrm Private HOME-Garage-RoofDeck Skyline view-EVTesla-PETS OK-Sleeps12

10.0 out of 10, Exceptional, (4)
"We were happy with the house- it’s as described and the location was great. Loved having the garage, not having to worry about finding parking "
HUGE! 3bdrm Private HOME-Garage-RoofDeck Skyline view-EVTesla-PETS OK-Sleeps12
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Far North Side
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Far North Side you may be interested in

Embassy Suites by Hilton Chicago Downtown River North

4.0 star property
8.4 out of 10, Very good, (3925)
"Happy Hour and breakfast was amazing. So much to choose from "
The price is HK$1,160
HK$1,361 total
includes taxes & fees
1 May - 2 May
Embassy Suites by Hilton Chicago Downtown River North

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2083)
"Excelente servicio en Palm restorant"
The price is HK$1,397
HK$1,867 total
includes taxes & fees
11 May - 12 May
Swissotel - Chicago

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2161)
"The only thing was the pool was closed. But other then that we had a good stay"
The price is HK$1,424
HK$1,671 total
includes taxes & fees
4 May - 5 May
Hilton Chicago/Magnificent Mile Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.