Be the first to submit a travel guide for Chicago

If you are a property owner or have stayed in a property in Chicago and wish to share valuable travel tips, interesting places to visit or activities to enjoy, please share them.

So why not write a short guide and have it published right here on Holiday-Rentals?

More information »

Self-catering holiday homes in Chicago

Refine Your Search Start a New Search
Find by availability dates:
and/or by weekly rental rate
(in £ GBP):
Current Criteria:
(remove all criteria)

Compare Selected
compare

Beautiful Brand-new Condo in trendy Andersonville

— Property 247326
Chicago condo rental - Open living room to kitchen floor plan
3 Bedrooms, Sleeps 8,
Condo, 2 Bathrooms, city centre, lake, jacuzzi
Rates - per property (GBP)
£122/night
£671/week
£2,439/month
Calendar Updated 23 Nov 2009

Property Review

I must give Dave top marks for communication, organization, and just being a pleasant guy to deal with. All the directions were clear, we arrived tired, at night, yet had no difficulties finding...
SPECIAL OFFER! Stay 4 nights and the 5th night is FREE! (12 November - 11 November)
compare

Wrigleyville/Southport Corridor Luxury Inn

— Property 203741
Special Offer
Chicago condo rental - Front Doors
2 Bedrooms, Sleeps 6,
Condo, 1 Bathroom, town, garden
Rates - per property (GBP)
£109/night
Calendar Updated 19 Nov 2009

Property Review

We spent close to a week in Chicago recently and were absolutely smitten with our home base - Chicago Southport Suite. Years ago, before I was married, I lived in Chicago. My husband and I...
compare

Duplex in Chicago city, 1 mile away from downtown

— Property 83872
Chicago apartment rental - Main bedroom
3 Bedrooms, Sleeps 8,
Apartment, 2 Bathrooms, 1 Separate Toilet, city centre, garden
Rates - per person (GBP)
£37 - £55/night
£218 - £326/week
compare

Magnificent Mile , Gold Coast Luxury Brownstone Downtown!

— Property 188897
Chicago property rental - Apt. 1- Living room w/fireplace, flatscreen
2 Bedrooms, Sleeps 6,
2 Bathrooms, city centre, lake, air-conditioning
Rates - per property (GBP)
£168 - £244/night
Calendar Updated 27 Oct 2009

Property Review

We had a wonderful stay at 57 E. Cedar. We were very comfortable and at home, and the neighborhood and location could not have been more ideal. We would definitely stay here again.
compare

ZEN Modern Luxury - steps from MagMile/Trump/Restaurants/Clubs

— Property 236933
Chicago condo rental - Living Room - Huge Windows, Spacious, Modern
1 Bedroom, Sleeps 6,
Condo, 1 Bathroom, city centre, lake, tennis court
Rates - per property (GBP)
£107 - £121/night
£793 - £853/week
Calendar Updated 27 Oct 2009

Property Review

My husband & I were looking for a celebration for our 2 boys big birthdays this year, 18 & 21, which would be memorable. We had a wonderful week in Chicago. The apartment is modern and very clean...
SPECIAL OFFER! **WOW** Walk to Everything Downtown**!! (19 November - 31 March)
compare

Wonderful 1bd/1ba Condo in Downtown Chicago. Walk to the Magnificent Mile!

— Property 263818
Special Offer
Chicago condo rental
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, city centre
Rates - per property (GBP)
£70 - £82/night
compare

ZEN Luxury Downtown Timber Loft - walk2 Oprah, SearsTower, United Center, Lake

— Property 240040
Chicago property rental - ZEN Bedroom
1 Bedroom, Sleeps 6,
1 Bathroom, city centre, lake, tennis court
Rates - per property (GBP)
£1,220/month
Calendar Updated 31 Aug 2009

Property Review

Myself and 4 friends stayed here for 4 days and had a brilliant time. The flat has everything that one needs and is located close to the city centre. The description was exactly as stated. The...
compare

Beautiful, Spacious & Sunny 3 Bedroom Condo

— Property 212128
3 Bedrooms/1 Bathroom, 1 Separate Toilet Apartment (Sleeps 8 city centre, town, balcony, air-conditioning, internet access, satellite or cable, TV, DVD, barbecue, starting at £152/night
compare

Beautiful Classic Brownstone Home

— Property 211715
5 Bedrooms/3 Bathrooms House (Sleeps 13 air-conditioning, internet access, satellite or cable, TV, DVD, starting at £262/night
compare

Amazing Views of the Chicago Skyline from this Luxury Condo

— Property 222038
2 Bedrooms/2 Bathrooms Condo (Sleeps 4 city centre, lake, balcony, fitness room, air-conditioning, internet access, satellite or cable, TV, DVD, starting at £70/night £442/week £1,372/month
compare

$$79 per Room - Unlimited Skyline Views in this New Contemporary Penthouse

— Property 265846
3 Bedrooms/2 Bathrooms Condo (Sleeps 6 city centre, jacuzzi, terrace, pets considered, air-conditioning, internet access, TV, DVD, starting at £976/week £2,744/month
compare

Truly Stunning Skyline/River Views! All Luxury Perfect Location w/Free Parking!

— Property 184807
2 Bedrooms/2 Bathrooms Condo (Sleeps 6 city centre, river, balcony, fitness room, air-conditioning, internet access, satellite or cable, TV, DVD, starting at £121/night £789/week
compare

$99 per night!! 2BR HOME BY LINCOLN SQUARE PERFECT LOCATION WALK TO TRAIN

— Property 184803
2 Bedrooms/1 Bathroom House (Sleeps 6 beach, city centre, communal pool, terrace, pets considered, air-conditioning, internet access, satellite or cable, TV, starting at £60/night £423/week
compare

$99 per Bedroom* 2BR-Spectacular Modern Corner Unit in an Amazing Location!

— Property 7011819h
2 Bedrooms/2 Bathrooms Apartment (Sleeps 6 air-conditioning, balcony, city centre, clothes dryer, dish washer, DVD, family, fridge, starting at £146/night
compare

$149* - Gorgeous Modern Condo in Heart of Downtown Mag Mile!

— Property 7011827h
1 Bedroom/1 Bathroom Condo (Sleeps 4 air-conditioning, balcony, beach, city centre, clothes dryer, cycling, dish washer, DVD
compare

$99 per Bedroom* 2BR -Awesome Loft! Walking Distance Downtown/Mag Mile

— Property 7011824h
2 Bedrooms/2 Bathrooms Condo (Sleeps 6 air-conditioning, city centre, clothes dryer, dish washer, DVD, family, fridge, historic, starting at £109/night
compare

$129 per Bedroom* 2BR- Gorgeous Condo w/ Incredible view Downtown/Michigan Ave

— Property 7011821h
2 Bedrooms/2 Bathrooms Condo (Sleeps 6 adventure, air-conditioning, beach, deck chairs, city centre, clothes dryer, cycling, wooden decking
compare

Great Value, Near Downtown & McCormick Place. Hot Tub, Amazing View, & Parking

— Property 225815
3 Bedrooms/1 Bathroom, 1 Separate Toilet Apartment (Sleeps 6 town, sauna, air-conditioning, internet access, satellite or cable, TV, DVD, parking, starting at £76/night £457/week
compare

Sp Suite MIllenum Park

— Property 144766
1 Bedroom/1 Bathroom Condo (Sleeps 2 city centre, lake, jacuzzi, balcony, fitness room, air-conditioning, internet access, satellite or cable, TV, starting at £79/night £488/week £1,402/month
compare
2 Bedrooms/2 Bathrooms Condo (Sleeps 6 air-conditioning, beach, city centre, clothes dryer, cycling, wooden decking, dish washer, DVD
compare

$129 per Beroom 1BR - Loop Timber Loft near Downtown/Michigan Ave/Grant Park

— Property 7011849h
1 Bedroom/1 Bathroom Condo (Sleeps 4 air-conditioning, city centre, clothes dryer, cycling, dish washer, family, fridge, iron & board
compare

4 BR - Gorgeous Contemporary Sleek Home

— Property 7011860h
4 Bedrooms/3 Bathrooms House (Sleeps 12 air-conditioning, city centre, clothes dryer, coffee grinder, cycling, wooden decking, dish washer, DVD, starting at £274/night
compare

Sp Suites Budget Rental

— Property 7017443h
Studio Apartment (Sleeps 2 air-conditioning, clothes dryer, fridge, kitchenette, linen provided, non smoking only, roller blading, stove top burners, starting at £46/night £274/week £732/month
compare

SP SUITES - North Side - Rogers Park -

— Property 7017444h
2 Bedrooms/1 Bathroom Apartment (Sleeps 4 air-conditioning, clothes dryer, dish washer, family, linen provided, microwave, non smoking only, oven, starting at £73/night £427/week £1,402/month
compare

SpSuites - Huron

— Property 7017445h
1 Bedroom/1 Bathroom Apartment (Sleeps 3 air-conditioning, balcony, clothes dryer, wooden decking, dish washer, family, fridge, grill, starting at £79/night £549/week £1,524/month
compare

SpSuites - Millenium Park

— Property 7017446h
1 Bedroom/1 Bathroom Apartment (Sleeps 3 air-conditioning, balcony, clothes dryer, dish washer, family, fridge, ice maker, iron & board, starting at £67/night £488/week £1,524/month
compare

SP SUITES - Streeterville

— Property 7020575h
1 Bedroom/1 Bathroom Apartment (Sleeps 3 accepts credit card, air-conditioning, balcony, beach, not necessary, central heating, city centre, coffee grinder, starting at £152/night £915/week £3,659/month
compare

$129 per Bedroom* 4BR - CONTEMPRARY HOME w/ Luxurious Finishes & Great Location

— Property 7006985h
4 Bedrooms/4 Bathrooms House (Sleeps 12 air-conditioning, beach, city centre, clothes dryer, cycling, wooden decking, dish washer, family
compare

$129 per Bedroom* 4 BR - Luxurious Multi-Level Downtown Home with Amazing Views!

— Property 7011615h
4 Bedrooms/4 Bathrooms, 1 Separate Toilet House (Sleeps 10 adventure, air-conditioning, city centre, clothes dryer, cycling, wooden decking, dish washer, DVD
compare

$89 per Bedroom* 3 BR -Breathtaking Graystone just Minutes from Wrigley Field

— Property 7011802h
3 Bedrooms/3 Bathrooms Condo (Sleeps 8 adventure, air-conditioning, balcony, blender, city centre, clothes dryer, cycling, dish washer