Hot Chicago Cottage Rates

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Featured Cottages in Chicago

6 Mi to Naval Base: Spacious Waukegan Home w/ Yard

6 Mi to Naval Base: Spacious Waukegan Home w/ Yard

3 out of 5
Waukegan
Stay at this 3-star cottage in Waukegan. Enjoy free parking, in-room fireplaces, and air conditioning. Popular attractions Six Flags Great America and Visual ...
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
Cozy Westmont Home: Walk to Metra Station!

Cozy Westmont Home: Walk to Metra Station!

3 out of 5
Westmont
Stay at this 3-star cottage in Westmont. Enjoy free parking and air conditioning. Popular attractions Twin Lakes Golf Course and Ty Warner Park are located ...
Cozy Westmont Home: Walk to Metra Station!
“The cottage” 2 bedrooms cozy and private home

“The cottage” 2 bedrooms cozy and private home

Markham
Stay at this cottage in Markham. Enjoy patios. Popular attractions Oak Hill Park and George Dunne National Golf Club are located nearby.
“The cottage” 2 bedrooms cozy and private home
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Country Club Hills Home: Walk to Rec Center!

Country Club Hills Home: Walk to Rec Center!

3 out of 5
Country Club Hills
Stay at this 3-star cottage in Country Club Hills. Enjoy free parking, patios, and air conditioning. Popular attractions Coyote Run Golf Course and Hollywood ...
Country Club Hills Home: Walk to Rec Center!
Classic Oak Park Home, 11 Mi to Downtown Chicago!

Classic Oak Park Home, 11 Mi to Downtown Chicago!

3 out of 5
Oak Park
Stay at this 3-star cottage in Oak Park. Enjoy free parking, patios, and in-room fireplaces. Popular attractions Frank Lloyd Wright Historic District and Garfield ...
Classic Oak Park Home, 11 Mi to Downtown Chicago!
Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!

Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!

3 out of 5
Oak Park
Stay at this 3-star cottage in Oak Park. Enjoy free parking and air conditioning. Popular attractions Frank Lloyd Wright Historic District and Portage Park are ...
Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!
Glendale Heights Home With Office and Backyard!

Glendale Heights Home With Office and Backyard!

3 out of 5
Glendale Heights
Stay at this 3-star cottage in Glendale Heights. Enjoy free parking and air conditioning. Popular attractions The Oasis Water Park and Bloomingdale Golf Club ...
Glendale Heights Home With Office and Backyard!
Des Plaines Vacation Rental w/ Spacious Backyard!

Des Plaines Vacation Rental w/ Spacious Backyard!

3 out of 5
Des Plaines
Stay at this 3-star cottage in Des Plaines. Enjoy in-room fireplaces and air conditioning. Popular attractions Allstate Arena and Rivers Casino are located ...
Des Plaines Vacation Rental w/ Spacious Backyard!
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!

8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!

3 out of 5
Oak Park
Stay at this 3-star cottage in Oak Park. Enjoy free parking and air conditioning. Popular attractions United Center and Frank Lloyd Wright Historic District ...
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
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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.

Chicago Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Chicago will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Chicago definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Chicago, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Chicago Cottages essential information

Accommodation
24 Cottages
Lowest Price
NZ$193
Highest Price
NZ$343
Popular accommodation
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard, Cozy Westmont Home: Walk to Metra Station!, “The cottage” 2 bedrooms cozy and private home, Country Club Hills Home: Walk to Rec Center!, Classic Oak Park Home, 11 Mi to Downtown Chicago!, Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!, Glendale Heights Home With Office and Backyard!, Des Plaines Vacation Rental w/ Spacious Backyard!, 8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!

Top trending hotels in Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$193 per night from 9 Jan to 10 Jan
NZ$193
includes taxes & fees
9 Jan - 10 Jan 2025
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$193 per night from 27 Jan to 28 Jan
NZ$193
includes taxes & fees
27 Jan - 28 Jan 2025
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$343 per night from 10 Jan to 11 Jan
NZ$343
includes taxes & fees
10 Jan - 11 Jan 2025
Book a stay at this eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our ...
Hyatt Regency Chicago
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Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
The price is NZ$230 per night from 7 Jan to 8 Jan
NZ$230
includes taxes & fees
7 Jan - 8 Jan 2025
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
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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.

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^Subject to availability and chosen travel dates.