Hot Chicago Cottage Rates

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Featured Cottages in Chicago

“The cottage” 2 bedrooms cozy and private home

“The cottage” 2 bedrooms cozy and private home

Markham
Located in Markham, this cottage is within a 10-minute drive of Advocate South Suburban Hospital and Oak Hill Park.
“The cottage” 2 bedrooms cozy and private home
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
With a stay at this cottage in Waukegan, you'll be a 4-minute drive from Lake Michigan and 8 minutes from Naval Base Great Lakes.
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
Beautiful+Serene+Upscale EcoGem by ALL the Action~>Beach+Lake+Ravinia+Train+Town

Beautiful+Serene+Upscale EcoGem by ALL the Action~>Beach+Lake+Ravinia+Train+Town

Highland Park
With a stay at this cottage in Highland Park, you'll be within a 5-minute drive of Lake Michigan and Moraine Park.
Beautiful+Serene+Upscale EcoGem by ALL the Action~>Beach+Lake+Ravinia+Train+Town
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2 Mi to Northwestern: Updated Home w/ Game Room!

2 Mi to Northwestern: Updated Home w/ Game Room!

3 out of 5
Evanston
With a stay at this cottage in Evanston, you'll be within a 10-minute drive of Northwestern University and Lake Michigan.
2 Mi to Northwestern: Updated Home w/ Game Room!
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!

Home w/ Fenced Yard: 13 Mi to Downtown Chicago!

3 out of 5
Evanston
With a stay at this cottage in Evanston, you'll be within a 5-minute drive of Lake Michigan and Loyola University Chicago.
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
Des Plaines Vacation Rental w/ Spacious Backyard!

Des Plaines Vacation Rental w/ Spacious Backyard!

3 out of 5
Des Plaines
With a stay at this cottage in Des Plaines (Oakton), you'll be a 3-minute drive from Allstate Arena and 7 minutes from Donald E. Stephens Convention Center.
Des Plaines Vacation Rental w/ Spacious Backyard!
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3 out of 5
Libertyville
Located in Libertyville, this cottage is within a 15-minute drive of Naval Base Great Lakes and Lake Michigan.
Riverfront Libertyville Retreat w/ Outdoor Kitchen
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
With a stay at this cottage in Oak Park, you'll be within a 10-minute drive of United Center and University of Illinois Chicago.
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
Cozy Westmont Home: Walk to Metra Station!

Cozy Westmont Home: Walk to Metra Station!

3 out of 5
Westmont
With a stay at this cottage in Westmont, you'll be within a 5-minute drive of Twin Lakes Park and Ty Warner Park.
Cozy Westmont Home: Walk to Metra Station!
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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
29 Cottages
Lowest Price
AU$173
Highest Price
AU$377
Popular accommodation
“The cottage” 2 bedrooms cozy and private home, 6 Mi to Naval Base: Spacious Waukegan Home w/ Yard, Beautiful+Serene+Upscale EcoGem by ALL the Action~>Beach+Lake+Ravinia+Train+Town, 2 Mi to Northwestern: Updated Home w/ Game Room!, Home w/ Fenced Yard: 13 Mi to Downtown Chicago!, Des Plaines Vacation Rental w/ Spacious Backyard!, Riverfront Libertyville Retreat w/ Outdoor Kitchen, 8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!, Cozy Westmont Home: Walk to Metra Station!

Top trending hotels in Chicago

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is AU$173 per night from 20 Apr to 21 Apr
AU$173
includes taxes & fees
20 Apr - 21 Apr
Located in Chicago (Downtown Chicago), Crowne Plaza Chicago West Loop by IHG is within a 15-minute walk of University of Illinois Chicago and Willis Tower.
Crowne Plaza Chicago West Loop by IHG
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$246 per night from 13 Apr to 14 Apr
AU$246
includes taxes & fees
13 Apr - 14 Apr
With a stay at Embassy Suites by Hilton Chicago Downtown River North, you'll be centrally located in Chicago, steps from State Street and 4 minutes by foot from ...
Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$377 per night from 16 Apr to 17 Apr
AU$377
includes taxes & fees
16 Apr - 17 Apr
A stay at Swissotel - Chicago places you in the heart of Chicago, within a 10-minute walk of Michigan Avenue and Millennium Park.
Swissotel - Chicago
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River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 20 Apr to 21 Apr
AU$185
includes taxes & fees
20 Apr - 21 Apr
With a stay at River Hotel, you'll be centrally located in Chicago, steps from Michigan Avenue and 5 minutes by foot from Chicago Riverwalk.
River 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.