Title:  Clearing Vacation Packages & Trips 2025 from $221 | Expedia.ca

  

[Hotels in Clearing](https://expedia.ca/Clearing-Chicago-Hotels.0-n6132083-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Clearing Car Rentals](https://expedia.ca/Car-Rentals-In-Clearing.d6132083.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Clearing Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

-   ## 
    
    Plan, book, travel with confidence
    

### 

Better together

Save up to CA $1,096 when you book a flight and hotel together\*

### 

Find the right fit

With over 300,000 hotels worldwide, it's easy to create a perfect package

### 

Rest easy

Plan, book, and manage your trip all in one place

## Top Holiday Package Deals in Clearing

Price found within the past 48 hours. Click for updated prices.

![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $655

per person

Nov 17 - Nov 20

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (291 reviews)

Had a great uneventful stay

Reviewed on Sep 22, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-17/2025-11-20/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=kQj7kHGMRi4nAKuYZ-keiQmXXIniTZHrTwr0to-UT7ilXAeLiGHKK1tmDEHF9Z8k)

![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Westin Michigan Avenue Chicago

Downtown Chicago

CA $864

per person

Dec 22 - Dec 26

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

8.8/10 Excellent! (1,046 reviews)

One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-22/2025-12-26/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=nOrgFANq-7NIqHnX3DG9wc2Hyc8C1PUT1pMU_wgxwR5jSNiZy8zIL-eqYqY_6K48)

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,252

per person

Nov 1 - Nov 4

found 2 days ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

Very accommodating and friendly staff, brilliant location

Reviewed on Oct 1, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-01/2025-11-04/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=D4WDtei-AbMIA4x6SUEvHGs4rXoBh7h6mD2B5EzNGaEQtNfczm-nKNDNEuH18Iso)

![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Park Hyatt Chicago

Downtown Chicago

CA $1,303

per person

Nov 3 - Nov 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,002 reviews)

Very friendly staff. Spacious rooms. Great location.

Reviewed on Oct 1, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-03/2025-11-06/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=Fmyq3uOpxWDvTShxD8KZ1IaoTC-YvIM7t7ZYjxxTGkvoXvG57muIh4efHnMZtUWP)

![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Swissotel - Chicago

Downtown Chicago

CA $775

per person

Nov 1 - Nov 4

found 2 days ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (2,765 reviews)

Everything was perfect!

Reviewed on Oct 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-01/2025-11-04/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=17288&paandie=true&dealMarker=D4WDtei-AbMIA4x6SUEvHLhW-uiGAFrR3nAU3zBm7yEpt6oCSSsm2ZRBBupLQdWc)

## Where to stay in Clearing

Find the best Clearing areas and neighborhoods for the activities you enjoy most. [Learn more about Clearing](https://expedia.ca/Chicago-Clearing.dx6132083)

![Downtown Chicago showing a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332072-Downtown-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

[Find hotel + flight trips in Downtown Chicago](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Chicago&DestID=6350699&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Magnificent Mile - River North](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24577-Magnificent-Mile.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

[Find hotel + flight trips in Magnificent Mile](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Magnificent%20Mile&DestID=800025&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![The Loop - Downtown featuring a river or creek](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192013-The-Loop-Downtown.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### The Loop

4.5/5(725 area reviews)

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

[Find hotel + flight trips in The Loop](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=The%20Loop&DestID=800024&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543369-chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

[Find hotel + flight trips in River North](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=River%20North&DestID=6350695&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Chicago which includes modern architecture and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54398-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Lincoln Park

5/5(20 area reviews)

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

[Find hotel + flight trips in Lincoln Park](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Lincoln%20Park&DestID=6059328&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Clearing Hotel Deals

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

CA $178

CA $209 total

Nov 2 - Nov 3

includes taxes & fees

7.8/10 Good! (9,387 reviews)

"Top Lage, sehr zentral"

Reviewed on Oct 1, 2025

[](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=6132083)

![Freehand Chicago](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Freehand Chicago

19 East Ohio Street, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $138

CA $227 total

Oct 27 - Oct 28

includes taxes & fees

7.8/10 Good! (2,412 reviews)

Good for 3 nights

"The price was right, the location excellent for shopping, riverwalk, other attractions within walking distance. The rooms are tiny, the bar and breakfast inconsistent. The mattress was terrible and needs to be replaced. The lobby area is beautifully refurbished and a place to spend time reading, ..."

Reviewed on Sep 30, 2025

[](https://expedia.ca/Hotel-Search?startDate=27%2F10%2F2025&endDate=28%2F10%2F2025&selected=9418281&PinnedHotelID=9418281&HadPinnedHotel=true&regionId=6132083)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $268

CA $314 total

Nov 2 - Nov 3

includes taxes & fees

8.4/10 Very Good! (5,029 reviews)

"staff friendly"

Reviewed on Sep 30, 2025

[](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true&regionId=6132083)

[See all 4,836 properties in Clearing](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F10%2F2025&endDate=04%2F10%2F2025&regionId=6132083)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does a Clearing vacation package cost?

> Handcraft your Clearing vacation package from an affordable CA $655. Pick from any combination of hotels, flights and rental cars to put together the escape you've been dreaming about for ages. Remember to add on one or two experiences!

### How do I get a cheap travel package to Clearing?

> Bundle your flights and hotels with Expedia to save big on your next getaway. With more than 550 air carriers and 1,000,000 properties globally, your Clearing vacation package can be customized exactly to suit your budget. With all those extra dollars, why not throw in one or more fun experiences and tours? It's an easy way to unlock even more bargains. The vacation you've always dreamed of in Clearing is closer than you thought!

### What are the top hotels in Clearing?

> Whether you're staying for one or several nights in Clearing, you'll get a wonderful night's rest at [Chicago Marriott Midway](https://www.expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information). This place is popular with lots of travelers.

### How far in advance should I book my Clearing vacation?

> Reserving your flight early with Expedia means one less thing to have to worry about. Many air carriers display prices up to 12 months prior to take off. Typically, this is the cheapest time to book. If circumstances have left you booking late, last-minute deals to Clearing sometimes occur in the weeks leading up to departure.

### What does an Expedia Clearing travel package include?

> Hotels, rental cars and flights, or any combination of them — it's up to you! Whether you're exploring Clearing with the entire family or enjoying a solo break, there's a package to match every style and budget. Once you've made your booking, why not add on a few tours and experiences?

### What should I know before booking a Clearing travel package?

> Our prices are already low. However, you'll enjoy even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.

### Can I choose my airline with a Clearing Expedia vacation package?

> Expedia offers access to more than 550 airline partners worldwide, so you sure can! Just select the airline you want and create your ideal Clearing escape.

### If I'm not able to travel, can I cancel my Clearing vacation package?

> If your travel plans in Clearing have changed, it's good to know that it is possible to cancel or amend your booking. If you booked in the last 24 hours, you may be eligible for a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose a fee. For more details, visit our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105).

### Discover the most popular places to visit in Clearing

![Wrigley Field featuring central business district, a city and a sporting event](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/35000/35620-Wrigley-Field.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

[](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction)

![Magnificent Mile - River North which includes signage, a city and night scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23728-Magnificent-Mile.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

[](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction)

![Navy Pier](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54738-Navy-Pier-Chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

[](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction)

### Things to do

![River tour boat in Chicago](https://mediaim.expedia.com/localexpert/170432/2ab44ef1-1211-4f4f-9436-ce9a14d4241f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Architecture River Tour

CA $67

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/architecture-river-tour.a170432.activity-details)

![Relax and enjoy the view](https://mediaim.expedia.com/localexpert/46106377/6686561e-a3aa-4cbf-9e71-f553bde2fa06.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago Architecture Center River Cruise aboard First Lady

CA $77

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/chicago-architecture-center-river-cruise-aboard-first-lady.a46106377.activity-details)

![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/1b6e1be3-a6ba-4b3d-8e57-4d0336c3fd23.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Color Factory Chicago Ticket

CA $47

per adult

**94%** of travellers recommend

[](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details)

[See all activities in Chicago](https://expedia.ca/things-to-do/search?rid=6132083)

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-   [Guest Houses in Summit](https://www.expedia.ca/Summit-Guest-Houses.d177671-aaGuestHouses.Travel-Guide-Accommodation)
-   [Hostels in Summit](https://www.expedia.ca/Summit-Hostels.d177671-aaHostels.Travel-Guide-Accommodation)
-   [Lgbt Friendly Hotels in Summit](https://www.expedia.ca/Summit-Hotels-LGBT-Friendly-Hotel.0-0-d177671-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Hotel Wedding Venues Hotels in Summit](https://www.expedia.ca/Summit-Hotels-Wedding-Hotels.0-0-d177671-tWeddingHotels.Travel-Guide-Filter-Hotels)
-   [Summit Hotels](https://www.expedia.ca/Summit-Hotels.d177671.Travel-Guide-Hotels)
-   [Resorts in Summit](https://www.expedia.ca/Summit-Resort-Hotels.d177671-aaResortHotels.Travel-Guide-Accommodation)
-   [Townhomes in Summit](https://www.expedia.ca/Summit-Townhomes.d177671-aaTownhomes.Travel-Guide-Accommodation)

-   [Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)
-   [Flights to Lyons](https://www.expedia.ca/Cheap-Flights-To-Lyons.d183188.Travel-Guide-Flights)
-   [Flights to McCook](https://www.expedia.ca/Cheap-Flights-To-McCook.d6132272.Travel-Guide-Flights)
-   [Flights from Midway Intl.](https://www.expedia.ca/lp/airports/mdw/flights-from-midway-intl-airport)
-   [Porter Airlines Toronto (YTZ) to Chicago (MDW) flights](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-billy-bishop-toronto-city-to-midway-intl/pd/ytz/mdw)
-   [Porter Airlines Ottawa (YOW) to Chicago (MDW) flights](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-macdonald-cartier-intl-to-midway-intl/pd/yow/mdw)
-   [Flights from Buffalo (BUF) to Chicago (MDW)](https://www.expedia.ca/lp/flights/buf/mdw/buffalo-to-chicago)
-   [Flights from Detroit (DTW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/dtw/mdw/detroit-to-chicago)
-   [Flights from South Bend (SBN) to Chicago (MDW)](https://www.expedia.ca/lp/flights/sbn/mdw/south-bend-to-chicago)
-   [Flights from Edmonton (YEG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yeg/mdw/edmonton-to-chicago)
-   [Flights from Hamilton (YHM) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yhm/mdw/hamilton-to-chicago)
-   [Flights from Halifax (YHZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yhz/mdw/halifax-to-chicago)
-   [Flights from Kelowna (YLW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ylw/mdw/kelowna-to-chicago)
-   [Flights from Ottawa (YOW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yow/mdw/ottawa-to-chicago)
-   [Flights from Windsor (YQG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqg/mdw/windsor-to-chicago)
-   [Flights from Thunder Bay (YQT) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqt/mdw/thunder-bay-to-chicago)
-   [Flights from Sudbury (YSB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ysb/mdw/sudbury-to-chicago)
-   [Flights from Timmins (YTS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yts/mdw/timmins-to-chicago)
-   [Flights from Toronto (YTZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago)
-   [Flights from Montreal (YUL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yul/mdw/montreal-to-chicago)
-   [Flights from Vancouver (YVR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yvr/mdw/vancouver-to-chicago)
-   [Flights from Winnipeg (YWG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ywg/mdw/winnipeg-to-chicago)
-   [Flights from Saskatoon (YXE) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yxe/mdw/saskatoon-to-chicago)
-   [Flights from North Bay (YYB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyb/mdw/north-bay-to-chicago)
-   [Flights from Calgary (YYC) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyc/mdw/calgary-to-chicago)
-   [Flights from Toronto (YYZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago)
-   [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago)

-   [Art Institute of Chicago](https://www.expedia.ca/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Vacation-Attraction)
-   [Blue Island Vacations](https://www.expedia.ca/Blue-Island.d80954.Destination-Travel-Guides)
-   [Broadview Vacations](https://www.expedia.ca/Broadview.d7064.Destination-Travel-Guides)
-   [Buckingham Fountain](https://www.expedia.ca/Buckingham-Fountain-Downtown-Chicago.d6064027.Vacation-Attraction)
-   [Burbank Vacations](https://www.expedia.ca/Burbank.d183178.Destination-Travel-Guides)
-   [Cibc Theatre](https://www.expedia.ca/CIBC-Theatre-Downtown-Chicago.d553248621563220853.Vacation-Attraction)
-   [Chatham Fields Vacations](https://www.expedia.ca/Chatham-Fields.d6132323.Destination-Travel-Guides)
-   [Chicago Museum of Science and Industry](https://www.expedia.ca/Chicago-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction)
-   [Chicago Vacations](https://www.expedia.ca/Chicago.d178248.Destination-Travel-Guides)
-   [Elmhurst Vacations](https://www.expedia.ca/Elmhurst.d7836.Destination-Travel-Guides)
-   [Ernest Hemingway Museum and House](https://www.expedia.ca/Ernest-Hemingway-Museum-And-House-Chicago.d6241604.Vacation-Attraction)
-   [Frank Lloyd Wright Historic District](https://www.expedia.ca/Frank-Lloyd-Wright-Historic-District-Chicago.d553248634340947645.Vacation-Attraction)
-   [Garfield Park Conservatory](https://www.expedia.ca/Garfield-Park-Conservatory-East-Garfield-Park.d6182807.Vacation-Attraction)
-   [Grant Park](https://www.expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction)
-   [Hillside Vacations](https://www.expedia.ca/Hillside.d8353.Destination-Travel-Guides)
-   [Hometown Vacations](https://www.expedia.ca/Hometown.d6132133.Destination-Travel-Guides)
-   [Loretto Hospital](https://www.expedia.ca/Loretto-Hospital-Austin.d553248635997986962.Vacation-Attraction)
-   [Melrose Park Vacations](https://www.expedia.ca/Melrose-Park.d8800.Destination-Travel-Guides)
-   [Millennium Park](https://www.expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction)
-   [Obama's House](https://www.expedia.ca/Obamas-House-Kenwood.d553248621533116333.Vacation-Attraction)
-   [Richard J. Daley Center](https://www.expedia.ca/Richard-J-Daley-Center-Downtown-Chicago.d6175173.Vacation-Attraction)
-   [River Forest Vacations](https://www.expedia.ca/River-Forest.d5986.Destination-Travel-Guides)
-   [Robie House](https://www.expedia.ca/Robie-House-Hyde-Park.d6064059.Vacation-Attraction)
-   [Sleepy Hollow Vacations](https://www.expedia.ca/Sleepy-Hollow.d6132427.Destination-Travel-Guides)
-   [South Loop Vacations](https://www.expedia.ca/South-Loop.d6130108.Destination-Travel-Guides)
-   [The East Bank Club](https://www.expedia.ca/The-East-Bank-Club-Downtown-Chicago.d553248621555594881.Vacation-Attraction)
-   [The Loop Vacations](https://www.expedia.ca/The-Loop.d800024.Destination-Travel-Guides)
-   [United Center](https://www.expedia.ca/United-Center-Near-West-Side.d6064077.Vacation-Attraction)
-   [Unity Temple](https://www.expedia.ca/Unity-Temple-Chicago.d6064079.Vacation-Attraction)
-   [Willis Tower](https://www.expedia.ca/Willis-Tower-Downtown-Chicago.d6064069.Vacation-Attraction)

-   [Rental cars Midway Intl. airport](https://www.expedia.ca/Car-Rentals-In-Midway-Intl.d5719117.Car-Rental-Guide)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.