Book Exclusive Chicago Vacation Packages

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Chicago flight + hotel packages

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

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was CA $1,386, price is now CA $1,006 per person
CA $1,006
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,843, price is now CA $1,260 per person
CA $1,260
per person
Aug 30 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,625, price is now CA $1,125 per person
CA $1,125
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,014, price is now CA $1,402 per person
CA $1,402
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $1,463, price is now CA $1,038 per person
CA $1,038
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.

Top Chicago hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $191 per night
CA $191
CA $227 total
Jun 29 - Jun 30
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Free cancellation
Reserve now, pay when you stay
The price is CA $189 per night
CA $189
CA $215 total
Jun 28 - Jun 29
includes taxes & fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Free cancellation
The price is CA $202 per night
CA $202
CA $240 total
Jun 30 - Jul 1
includes taxes & fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $291 per night
CA $291
CA $342 total
Jul 4 - Jul 5
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $215 per night
CA $215
CA $256 total
Jun 29 - Jun 30
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $195 per night
CA $195
CA $232 total
Jun 30 - Jul 1
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 staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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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.

Popular places to visit

Wrigley Field

Wrigley Field

4.5/5(159 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(3 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(460 reviews)

With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Navy Pier

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 $1,006. 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.

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