Book Exclusive Chicago Vacation Packages

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Chicago flight + hotel packages

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

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 23 - May 26
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Dorothy's

Dorothy's

3 out of 5
Lakeview
Save 100% on your flight
per person
Jul. 5 - Jul. 8
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 3-star B&B in Chicago. Enjoy free breakfast, free WiFi, and laundry facilities. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 20 - Jun. 23
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 13 - Jun. 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

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.

Michigan Avenue
McCormick Place

McCormick Place

4.5/5(141 reviews)

During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.

McCormick Place

Frequently asked questions

How much are vacation packages to Chicago?
Get ready to be surprised — you can vacation in Chicago for as low as CA $879. At Travelocity, we save you money and hassle with our excellent vacation packages. With hotels, flights and tours all in one place, why wait any longer?
How long should my Chicago vacation be?
Typically, 2 nights is what most tourists book for their Chicago trip. That’s a good starting point, but there’s plenty more to discover if you allow yourself a little longer.
Where can I get the best vacation package deals for Chicago?
Picking up the best package deal to Chicago is a piece of cake with Travelocity. With 400 air carriers and 1,000,000 properties all over the world, you’re spoiled for choice when it comes to your hotels and flights.
Why should I purchase my Chicago vacation bundle via Travelocity?
Because you’ll never roam alone if you book with us, and we offer round-the-clock support and exceptional service to boot. Add to that our Price Match Guarantee and tons of destinations to pick from. It’s our job to make your daydreams a reality.
Can I save money on my Chicago car rental if I bundle it with hotels and flights?
Absolutely — combine your flight, car and hotel into a Chicago vacation package and you can save a tidy sum. With so much to see in Chicago, having your own wheels will make exploring a joy. Once you’ve buckled yourself in, hit the wide open road and cruise toward Six Flags Great America, a famous attraction roughly 56 kilometers from Chicago.
Which airport is best for Chicago?
O’Hare Intl. Airport (ORD) (26 kilometers away from downtown), Midway Intl. Airport (MDW) (14 kilometers away from central Chicago) and Lewis University Airport (LOT) (48 kilometers away from central Chicago) are the main hubs in Chicago.
What is there to do in Chicago?
While hopping off the tourist trail is rewarding, you really shouldn’t miss the popular sights that make a place famous. Wrigley Field and Six Flags Great America are a couple of them in Chicago.
Where should I stay when visiting Chicago?
If you’re after someplace comfortable to lay your head, have a look at the Congress Plaza Hotel. It’s the top choice for many visitors.
Chicago showing a high-rise building and a city as well as a family
Chicago featuring heritage elements, signage and a high-rise building
Chicago
Chicago which includes street scenes and a skyscraper as well as a family
Willis Tower which includes central business district, a high-rise building and a city