Chicago Vacations 2026/2026 from CA $812

Chicago flight + hotel packages

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

The Emily Hotel

Downtown Chicago

CA $812

per person

Jan 9 - Jan 13

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Book a stay at this business-friendly 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 United Center and Chicago Riverwalk are located nearby.

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $861

per person

Mar 6 - Mar 8

found 7 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Chicago luxury home suites

Downtown Chicago

CA $2,782

per person

Feb 25 - Mar 1

found 1 day ago

Roundtrip non-stop flight included

St. John's (YYT) to Chicago (ORD)

Stay at this aparthotel in Chicago. Enjoy free WiFi and housekeeping. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $920

per person

Feb 25 - Mar 1

found 1 day ago

Roundtrip non-stop flight included

St. John's (YYT) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Level Chicago – Old Town

Downtown Chicago

CA $1,020

per person

Feb 25 - Mar 1

found 1 day ago

Roundtrip non-stop flight included

St. John's (YYT) 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

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

CA $127

CA $150 total

Dec 18 - Dec 19

includes taxes & fees

Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Pool

Breakfast included

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $147

CA $172 total

Dec 17 - Dec 18

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.

Pet-friendly

Free WiFi

Silversmith Hotel Chicago Downtown

10 S Wabash Ave Chicago IL

Free cancellation

Reserve now, pay when you stay

Get rates

Book a stay at this business-friendly 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 Millennium Park and Chicago Riverwalk are located nearby.

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $153

CA $215 total

Dec 21 - Dec 22

includes taxes & fees

Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Club Quarters Hotel Wacker at Michigan, Chicago

75 E Wacker Dr Chicago IL

Free cancellation

Reserve now, pay when you stay

Get rates

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Pet-friendly

Free WiFi

Eurostars Magnificent Mile

660 North State Street Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $130

CA $152 total

Jan 8 - Jan 9, 2026

includes taxes & fees

Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.

Spa

Free WiFi

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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

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.

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 acclaimed theater scene in this vibrant area.

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 theater scene and notable monuments in this vibrant area.

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 $812. 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.