Chicago Vacations 2025 from CA $521

Chicago flight + hotel packages

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

Red Roof Inn Chicago - Alsip

per person

Apr. 22 - Apr. 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (MDW)

Stay at this hotel in Alsip. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Hollywood Park and Gaelic Park are located nearby.

Ruby Room

West Town

per person

Apr. 22 - Apr. 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a garden, and concierge services. Popular attractions Michigan Avenue and Millennium Park are located nearby.

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Save 100% on your flight

per person

Apr. 22 - Apr. 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Stay at this 4-star 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.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

per person

May 4 - May 9

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Chicago (ORD)

Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Theatre and Chicago Riverwalk are located nearby.

Hilton Chicago/Oak Brook Suites

per person

Apr. 22 - Apr. 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this business-friendly hotel in Villa Park. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Drury Lane Theater and Oakbrook Center Mall 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 $122

CA $143 total

includes taxes & fees

17 Feb - 18 Feb

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 Millennium Park and Michigan Avenue are located nearby.

Free WiFi

Restaurant

L7 Chicago by LOTTE

225 N Wabash Ave, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $179

CA $210 total

includes taxes & fees

17 Feb - 18 Feb

Book a stay at this boutique 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 Michigan Avenue are located nearby.

Pet-friendly

Free WiFi

Hilton Chicago

720 S Michigan Ave, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $211

CA $289 total

includes taxes & fees

22 Feb - 23 Feb

Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Michigan Avenue are located nearby.

Pool

Pet-friendly

Pendry Chicago

230 North Michigan Avenue, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $234

CA $333 total

includes taxes & fees

9 Mar - 10 Mar

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 Millennium Park and Michigan Avenue are located nearby.

Pet-friendly

Free WiFi

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $145

CA $170 total

includes taxes & fees

19 Feb - 20 Feb

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

Hyatt Regency Schaumburg Chicago

1800 East Golf Rd, Schaumburg, IL

Free cancellation

Reserve now, pay when you stay

CA $125

CA $144 total

includes taxes & fees

17 Feb - 18 Feb

Stay at this 4-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and LEGOLAND® Discovery Center are located nearby.

Pool

Parking included

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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 theater scene in this vibrant area.

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.

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.

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 $521. 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.