Search Chicago Cottage Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Cottages in Chicago

We don't have any properties that match your exact search

Recommended hotels in Chicago

The Chicago Hotel Collection Ambassador Gold Coast

4.0 star property
8.2 out of 10, Very Good, (1007)
"Great Front desk staff! All staff was very friendly and location was wonderful 😀"
The price is ¥813
¥24,599 total
includes taxes & fees
Jul 6 - Jul 7
The Chicago Hotel Collection Ambassador Gold Coast

citizenM Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (3261)
"Amazing hotel"
The price is ¥20,063
¥23,551 total
includes taxes & fees
Jul 7 - Jul 8
citizenM Chicago Downtown

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2052)
"Amazing stay"
The price is ¥30,982
¥40,543 total
includes taxes & fees
Jul 6 - Jul 7
Sable at Navy Pier Chicago, Curio Collection by Hilton

Claridge House

4.0 star property
8.8 out of 10, Excellent, (1239)
"Good location, nice area"
The price is ¥11,017
¥17,156 total
includes taxes & fees
Jul 7 - Jul 8
Claridge House

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (8936)
"Great location, beautiful hotel "
The price is ¥17,137
¥20,119 total
includes taxes & fees
Jul 7 - Jul 8
Congress Plaza Hotel

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.2 out of 10, Good, (1090)
"We enjoyed our time at this stay. "
The price is ¥608
¥24,358 total
includes taxes & fees
Jul 6 - Jul 7
The Chicago Hotel Collection - Magnificent Mile

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2015)
"The great place to stayed if you are traveling alone"
The price is ¥12,663
¥17,390 total
includes taxes & fees
Jul 7 - Jul 8
Freehand Chicago

Hotel Felix River North/Magnificent Mile

4.0 star property
8.2 out of 10, Very Good, (1821)
"Great price, great location, small but nice rooms!"
The price is ¥32,505
¥42,550 total
includes taxes & fees
Jul 11 - Jul 12
Hotel Felix River North/Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very Good, (1639)
"Great stay"
Hotel Saint Clair- Magnificent Mile

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1000)
"Reasonably priced, cleanliness of room, restaurant and bar within, and staff was friendly. Would highly recommend this Hotel! "
The price is ¥16,392
¥19,243 total
includes taxes & fees
Jul 6 - Jul 7
Best Western River North Hotel

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3023)
"Enjoyed the stay "
The price is ¥20,654
¥24,246 total
includes taxes & fees
Jul 3 - Jul 4
Eurostars Magnificent Mile

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4317)
"The hotel was great from the staff to the location "
The price is ¥20,006
¥23,485 total
includes taxes & fees
Jul 3 - Jul 4
River Hotel

InterContinental Chicago Magnificent Mile by IHG

4.5 star property
9.0 out of 10, Wonderful, (1956)
"Had a great stay! The room was clean and comfortable, staff were friendly and helpful, and the location was convenient for everything I needed. Would definitely stay here again. "
The price is ¥27,419
¥36,793 total
includes taxes & fees
Jul 10 - Jul 11
InterContinental Chicago Magnificent Mile by IHG

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
8.6 out of 10, Excellent, (2408)
"Great hotel"
The price is ¥19,234
¥25,103 total
includes taxes & fees
Jul 3 - Jul 4
La Quinta Inn & Suites by Wyndham Chicago Downtown

The Chicago Hotel Collection River North

3.0 star property
7.2 out of 10, Good, (503)
"The accommodations were okay"
The price is ¥6,024
¥22,266 total
includes taxes & fees
Jul 3 - Jul 4
The Chicago Hotel Collection River North

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2322)
"It was a great stay! "
The price is ¥23,012
¥31,237 total
includes taxes & fees
Jul 6 - Jul 7
Swissotel - Chicago

Ohio House Motel

2.5 star property
9.0 out of 10, Wonderful, (1015)
"Great place to stay!"
The price is ¥17,479
¥20,517 total
includes taxes & fees
Jul 8 - Jul 9
Ohio House Motel

The Godfrey Hotel Chicago

4.5 star property
8.6 out of 10, Excellent, (1875)
"We really enjoyed the beautiful ambiance of the property, especially the rooftop bar at night, which offered a perfect setting to unwind."
The price is ¥21,371
¥28,455 total
includes taxes & fees
Jul 7 - Jul 8
The Godfrey Hotel Chicago

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1862)
"Very historic place, nice rooms, staff was helpful, great for a short stay"
The price is ¥18,279
¥24,837 total
includes taxes & fees
Jul 7 - Jul 8
Millennium Knickerbocker Chicago

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2220)
"Great place to stay!"
The price is ¥14,716
¥17,275 total
includes taxes & fees
Jul 7 - Jul 8
Travelodge by Wyndham Downtown Chicago
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.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Why book your cottage in Chicago with Expedia?
Expedia has some wonderful cottages in Chicago, so start packing for an unforgettable vacation on nature's doorstep. If you need to stick to a budget, click on how much you'd like to spend and your preferred property star rating. Or, make the most of our filters to search for cottages with free WiFi or a pool. We'll help you find the perfect fit whatever your style of travel or plans.
How can I find cheap cottages in Chicago?
An excellent way to compare cheap cottages in Chicago is with Expedia's user-friendly filter tool. Refine your search results by amenities, budget and star rating to take advantage of awesome bargains with only a few clicks.
What is there to do in Chicago near my cottage?
Chicago has enough activities and experiences to keep you going for weeks, beginning with Anna and Frederick Douglass Park. Grant Park, Marquette Park and Midway Plaisance are other popular attractions. If you're hanging around a while, Ernest Hemingway Museum and House and Bridgehouse and Chicago River Museum are great additions to your itinerary.