Hot Chicago Cottage Rates

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Featured Cottages in Chicago

Pet-friendly Abode, 2 Mi to Dtwn Evanston!

Pet-friendly Abode, 2 Mi to Dtwn Evanston!

3 out of 5
Evanston, IL
Stay at this 3-star cottage in Evanston. Enjoy free parking and air conditioning. Popular attractions Wrigley Field and Baha'i House of Worship are located ...
Opens in a new windowPet-friendly Abode, 2 Mi to Dtwn Evanston!
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 Genesee ...
Opens in a new window6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
Game Nights, Bbqs & Family Fun: Chicago Area Hub

Game Nights, Bbqs & Family Fun: Chicago Area Hub

3 out of 5
Des Plaines
Stay at this 3-star cottage in Des Plaines. Enjoy free parking, in-room fireplaces, and air conditioning. Popular attractions Allstate Arena and Lake Park are ...
Opens in a new windowGame Nights, Bbqs & Family Fun: Chicago Area Hub
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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
Stay at this 3-star business-friendly cottage in Evanston. Enjoy free parking and air conditioning. Popular attractions Baha'i House of Worship and Milwaukee ...
Opens in a new window2 Mi to Northwestern: Updated Home w/ Game Room!
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 Walt ...
Opens in a new windowClassic 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 business-friendly cottage in Oak Park. Enjoy free parking and air conditioning. Popular attractions Frank Lloyd Wright Historic District ...
Opens in a new windowOak Park Home w/ Fire Pit - 5 Mi to Garfield Park!
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 Park and Ty Warner Park are located nearby.
Opens in a new windowCozy Westmont Home: Walk to Metra Station!
Home w/ Office + Yard: 25 Mi to Downtown Chicago!

Home w/ Office + Yard: 25 Mi to Downtown Chicago!

3 out of 5
696 Crescent Ct, Glen Ellyn, IL
Stay at this 3-star cottage in Glen Ellyn. Enjoy free parking, patios, and in-room fireplaces. Popular attractions Lilacia Park and Dupage County Historical ...
Opens in a new windowHome w/ Office + Yard: 25 Mi to Downtown Chicago!
The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!

The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!

Highwood, IL
Book a stay at this family-friendly cottage in Highwood. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Moraine Park and Park Avenue ...
Opens in a new windowThe Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!
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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
28 Cottages
Lowest Price
NZ$207
Highest Price
NZ$423
Popular accommodation
Pet-friendly Abode, 2 Mi to Dtwn Evanston!, 6 Mi to Naval Base: Spacious Waukegan Home w/ Yard, Game Nights, Bbqs & Family Fun: Chicago Area Hub, 2 Mi to Northwestern: Updated Home w/ Game Room!, Classic Oak Park Home, 11 Mi to Downtown Chicago!, Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!, Cozy Westmont Home: Walk to Metra Station!, Home w/ Office + Yard: 25 Mi to Downtown Chicago!, The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!

Top trending hotels in Chicago

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 NZ$242 per night from 23 Nov to 24 Nov
NZ$242
23 Nov - 24 Nov
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
Opens in a new windowEmbassy Suites by Hilton Chicago Downtown River North
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$423 per night from 6 Nov to 7 Nov
NZ$423
6 Nov - 7 Nov
includes taxes & fees
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 ...
Opens in a new windowCongress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$207 per night from 17 Nov to 18 Nov
NZ$207
17 Nov - 18 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Opens in a new windowHilton Chicago/Magnificent Mile Suites
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citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$234 per night from 19 Nov to 20 Nov
NZ$234
19 Nov - 20 Nov
includes taxes & fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
Opens in a new windowcitizenM Chicago Downtown
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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.