Chicago Vacations 2025/2026 from CA $641

Chicago flight + hotel packages

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

Pendry Chicago

Downtown Chicago

Save 100% on your flight

per person

Sep 27 - Sep 29

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

per person

Sep 23 - Sep 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) 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.

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Downtown Chicago

Save 100% on your flight

per person

Sep 24 - Sep 29

found 5 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 27 - Aug 31

found 18 hours ago

Roundtrip flight included

Edmonton (YEG) 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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Renaissance Chicago O'Hare Suites Hotel

O'Hare

Save 100% on your flight

per person

Oct 5 - Oct 11

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this 4-star 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.

Top Chicago hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $243

CA $285 total

Aug 4 - Aug 5

includes taxes & fees

Book a stay at this business-friendly 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 Grant Park and Art Institute of Chicago are located nearby.

Free WiFi

Restaurant

InterContinental Chicago Magnificent Mile by IHG

505 N Michigan Ave, Chicago, IL

CA $273

CA $364 total

Aug 10 - Aug 11

includes taxes & fees

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Pool

Spa

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $207

CA $243 total

Aug 10 - Aug 11

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

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $288

CA $339 total

Aug 10 - Aug 11

includes taxes & fees

Stay at this 4-star 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

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street, Chicago, IL

Free cancellation

CA $202

CA $237 total

Aug 10 - Aug 11

includes taxes & fees

Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Pet-friendly

Free WiFi

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

CA $226

CA $265 total

Aug 11 - Aug 12

includes taxes & fees

Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Free WiFi

Restaurant

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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

4.5/5(158 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.

Navy Pier

4.5/5(459 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.

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.

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 $641. 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.