Title: Westchester Vacation Rentals from CA $130: Short-Term Rentals for 2026 | Expedia.ca

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![Schiller Woods view in Chicago of Illinois](https://images.trvl-media.com/place/7758/5dc6d33e-4d46-4f37-9026-58124815a2a3.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Westchester Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Westchester vacation rentals

![Business centre](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/825d44e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cafe](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/715d8399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/f7e5c565_edited_04eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/0480d64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Downtown Chicago

[](https://www.expedia.ca/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

9.6/10

Exceptional

(182)

"Awesome stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sally

[](https://www.expedia.ca/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/a9b3121a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio, 1 Queen Bed (Studio Apartment) | Private kitchen](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/1bf06d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ccaab668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/eacd6d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Downtown Chicago

[](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

9.2/10

Wonderful

(1032)

"Place was very nice and clean. We enjoyed the stay there. Will book it again when we come back to Chicago visit again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Khalid

CA $150

CA $217 total

includes taxes & fees

Jan 5 - Jan 6

[](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/cb208a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/9bdb478c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 Single Bed, City View | Living area](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/f7ca0ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Downtown Chicago

[](https://www.expedia.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

9.0/10

Wonderful

(408)

"Great location, clean room and friendly staff!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott

[](https://www.expedia.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/44167e80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Duplex, City View](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/bd7ffa4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/27e8c783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Duplex, City View | Shared kitchen](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/14e4f60e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Downtown Chicago

[](https://www.expedia.ca/Chicago-Hotels-Chicago-Luxury-Home-Suites.h121424489.Hotel-Information)

10/10

Exceptional

(4)

"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Alex

CA $145

CA $171 total

includes taxes & fees

Jan 14 - Jan 15

[](https://www.expedia.ca/Chicago-Hotels-Chicago-Luxury-Home-Suites.h121424489.Hotel-Information)

![Studio | Private kitchen](https://images.trvl-media.com/lodging/89000000/88910000/88902500/88902456/42e169d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio](https://images.trvl-media.com/lodging/89000000/88910000/88902500/88902456/380b6682.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Exterior](https://images.trvl-media.com/lodging/89000000/88910000/88902500/88902456/97ca7dfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Interior](https://images.trvl-media.com/lodging/89000000/88910000/88902500/88902456/caa9b8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in West Town

[](https://www.expedia.ca/Chicago-Hotels-The-Perfect-Home-Away-From-Home-For-Your-Romantic-Urban-Getaway-747-Lofts-Cabin-307-Hotel-Room.h88902456.Hotel-Information)

9.0/10

Wonderful

(17)

"Loved the space and location "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Caroline

CA $102

CA $474 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Chicago-Hotels-The-Perfect-Home-Away-From-Home-For-Your-Romantic-Urban-Getaway-747-Lofts-Cabin-307-Hotel-Room.h88902456.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/06060406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3e6dada5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/2626f596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/c25a1316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Lakeview

[](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information)

9.6/10

Exceptional

(27)

"Nice place "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Barry

CA $111

CA $130 total

includes taxes & fees

Jan 5 - Jan 6

[](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information)

![Business Apartment, City View | Private kitchen](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/0374aa13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, City View](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/6a748c36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/c94fe51a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![City Apartment, City View | Living area](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/7fc927d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ENVITAE Hotel 4 Bedroom Luxury Apartments

[](https://www.expedia.ca/Chicago-Hotels-4BR-Corporate-Suite-Central-And-Modern.h118632066.Hotel-Information)

9.4/10

Exceptional

(10)

"Good for family, enjoyed the stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Karthik

CA $1,230

CA $1,732 total

includes taxes & fees

Jan 5 - Jan 6

[](https://www.expedia.ca/Chicago-Hotels-4BR-Corporate-Suite-Central-And-Modern.h118632066.Hotel-Information)

![Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/acb706d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio Suite, 1 Double Bed, Kitchen (Washer/Dryer)](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/fe592b2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom, Kitchen (Washer/Dryer) | Private kitchen](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/38d26f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/a77496eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Downtown Evanston

[](https://www.expedia.ca/Chicago-Hotels-The-Gem-Museum-Suites.h103465448.Hotel-Information)

9.4/10

Exceptional

(101)

"Lovely "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Duncan

CA $249

CA $285 total

includes taxes & fees

Jan 5 - Jan 6

[](https://www.expedia.ca/Chicago-Hotels-The-Gem-Museum-Suites.h103465448.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121340000/121330200/121330192/7db98038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121340000/121330200/121330192/2e0ddd03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121340000/121330200/121330192/df9330f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121340000/121330200/121330192/ee4be839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Forest Park

[](https://www.expedia.ca/Chicago-Hotels-Classic-Forest-Park-Foursquare-1-Mi-To-Blue-Line.h121330192.Hotel-Information)

CA $213

CA $562 total

includes taxes & fees

Jan 31 - Feb 1

[](https://www.expedia.ca/Chicago-Hotels-Classic-Forest-Park-Foursquare-1-Mi-To-Blue-Line.h121330192.Hotel-Information)

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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## Top Westchester Hotel Reviews

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg)

### Hilton Chicago

10/10 Excellent

"Nice pillows"

[](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information)

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg)

### Palmer House a Hilton Hotel

10/10 Excellent

"Dolores was incredible and our room was gorgeous! "

[](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information)

![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg)

### River Hotel

10/10 Excellent

"I was there for the new years celebrations downtown. The hotel was very clean and organized. The security was also very attentive. They were checking people at the door and making sure that only registered guest came in which made me feel at ease, and at night the noice control was super quiet. For that festive occasion it was very controlled. "

[](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent

"The view really makes this hotel worth it! The bench in my room was a bit worn but other than that nice hotel and great stay "

[](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

![InterContinental Chicago Magnificent Mile by IHG](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg)

### InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"The room was spacious with a great view. The bathroom was also plenty bug. 4 of us stayed comfortably for the night. The fitness center is great, if a bit warm, and the pool is excellent. Location is also perfect."

[](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information)

![Holiday Inn Chicago Dwtn - The Mart by IHG](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344_y.jpg)

### Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent

"Great view of downtown Chicago, easy access to the Mart, and friendly/helpful staff "

[](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information)

![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg)

### Silversmith Hotel Chicago Downtown

10/10 Excellent

"."

[](https://expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Staff was great, clean, nice bed"

[](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information)

![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg)

### Hyatt Regency Chicago

10/10 Excellent

"Wonderful breakfast. Friendly and professionally competent staff!"

[](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information)

## Find out more about Westchester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Westchester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Big White Ski Resort Vacation Rentals ](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals)
- [Ontario Vacation Rentals ](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations)
- [British Columbia Vacation Rentals ](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations)
- [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Apartments in Westchester ](https://expedia.ca/Westchester-Apartments.d7758-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in Westchester ](https://expedia.ca/Westchester-Private-Vacation-Homes.d7758-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Westchester ](https://expedia.ca/Westchester-Condos.d7758-aaCondos.Travel-Guide-Accommodation)
- [Aparthotels in Westchester ](https://expedia.ca/Westchester-Apart-Hotels.d7758-aaApartHotels.Travel-Guide-Accommodation)
- [Motels in Westchester ](https://expedia.ca/Westchester-Motels.d7758-aaMotels.Travel-Guide-Accommodation)
- [Cottages in Westchester ](https://expedia.ca/Westchester-Cottages.d7758-aaCottages.Travel-Guide-Accommodation)
- [B&B in Westchester ](https://expedia.ca/Westchester-Bed-And-Breakfast.d7758-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Westchester ](https://expedia.ca/Westchester-Guest-Houses.d7758-aaGuestHouses.Travel-Guide-Accommodation)
- [Hostels in Westchester ](https://expedia.ca/Westchester-Hostels.d7758-aaHostels.Travel-Guide-Accommodation)
- [Villas in Westchester ](https://expedia.ca/Westchester-Villas.d7758-aaVillas.Travel-Guide-Accommodation)
- [Resorts in Westchester ](https://expedia.ca/Westchester-Resort-Hotels.d7758-aaResortHotels.Travel-Guide-Accommodation)
- [Houseboats in Westchester ](https://expedia.ca/Westchester-Houseboats.d7758-aaHouseboats.Travel-Guide-Accommodation)
- [Residences in Westchester ](https://expedia.ca/Westchester-Residences.d7758-aaResidences.Travel-Guide-Accommodation)
- [Farmstay in Westchester ](https://expedia.ca/Westchester-Agritourism.d7758-aaAgritourism.Travel-Guide-Accommodation)
- [Cabin Rentals in Westchester ](https://expedia.ca/Westchester-Cabins.d7758-aaCabins.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Westchester?

### What are some of the best vacation rentals that Westchester has to offer?

### How many vacation rentals are there in Westchester?

### What can I see and do in Westchester?

### What are vacation rentals like in Westchester?

### Expedia's Latest Trends

Hotels

- [Best Hotels in Schaumburg](https://expedia.ca/Schaumburg-Hotels.d8107.Travel-Guide-Hotels)
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- [Hotel Quartier Latin Montréal](https://expedia.ca/Montreal-Hotels-Hotel-Quartier-Latin-Montreal.h890030.Hotel-Information)
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Flights

- [Flights from Toronto to Dubai](https://expedia.ca/lp/flights/yyz/dxb/toronto-to-dubai)
- [Flights to Dollar](https://expedia.ca/Cheap-Flights-To-Dollar.d6193375.Travel-Guide-Flights)
- [Flights to Rosemont](https://expedia.ca/Cheap-Flights-To-Rosemont.d7581.Travel-Guide-Flights)

Activities

- [Things to do in Des Plaines](https://expedia.ca/Things-To-Do-In-Des-Plaines.d7863.Travel-Guide-Activities)
- [Things to do in New York](https://expedia.ca/Things-To-Do-In-New-York.d178293.Travel-Guide-Activities)

Packages

- [Navy Pier](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction)
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- [Willis Tower](https://expedia.ca/Willis-Tower-Downtown-Chicago.d6064069.Vacation-Attraction)
- [Griffin Museum of Science and Industry](https://expedia.ca/Griffin-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction)
- [Golf Trip](https://expedia.ca/Golf.d6132095.Destination-Travel-Guides)
- [Grant Park](https://expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction)

General

- [Visit Evanston](https://expedia.ca/Evanston.dx8049)
- [Visit Schaumburg](https://expedia.ca/Schaumburg.dx8107)
- [Visit Elk Grove Village](https://expedia.ca/Elk-Grove-Village.dx7833)

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