Chicago Vacations 2026 from CA $1,027

Chicago flight + hotel packages

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

CA $1,027

per person

Sep 3 - Sep 7

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, 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.

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

CA $1,148

per person

Jul 15 - Jul 19

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

Stay at this 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

Downtown Chicago

CA $1,125

per person

Aug 16 - Aug 21

found 22 hours 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 Fulton Market

Downtown Chicago

CA $1,465

per person

Jul 15 - Jul 19

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Level Chicago – Old Town

Downtown Chicago

CA $1,807

per person

Aug 5 - Aug 9

found 1 day ago

Roundtrip non-stop 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.

Top Chicago hotels deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $190

CA $226 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

9300 Bryn Mawr Ave Rosemont IL

Free cancellation

Reserve now, pay when you stay

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.

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $291

CA $341 total

Jul 3 - Jul 4

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 - Magnificent Mile

166 E Superior Street Chicago IL

Free cancellation

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.

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $215

CA $256 total

Jul 1 - Jul 2

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.

Hotel Felix River North/Magnificent Mile

111 W Huron St Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $201

CA $285 total

Jul 5 - Jul 6

includes taxes & fees

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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.

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 $1,027. 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.