Downtown Chicago Vacation Packages

Top Holiday Package Deals in Downtown Chicago

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

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

CA $777

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

8.6/10 Excellent! (1,007 reviews)

It was a wonderful experience.

Reviewed on Jul 16, 2026

Level Chicago – Old Town

Downtown Chicago

CA $1,436

per person

Aug 24 - Aug 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (497 reviews)

Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.

Reviewed on Jul 14, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $1,110

per person

Sep 24 - Sep 27

found 8 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (512 reviews)

Hampton Inn & Suites Chicago Medical District UIC

Near West Side

CA $1,029

per person

Aug 24 - Aug 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (657 reviews)

Hotel Felix River North/Magnificent Mile

Downtown Chicago

CA $1,635

per person

Oct 10 - Oct 14

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.2/10 Very good! (2,809 reviews)

Queen is very small but nice staff

Reviewed on Jul 16, 2026

Where to stay in Downtown Chicago

Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Chicago

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

Downtown Chicago Hotel Deals

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

CA $272

CA $324 total

Aug 3 - Aug 4

includes taxes & fees

8.2/10 Very good! (1,756 reviews)

"Great service, valet’s great too, loved how we were able to walk to night life"

Reviewed on Jul 16, 2026

Omni Chicago Hotel

676 N Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

CA $375

CA $492 total

Jul 26 - Jul 27

includes taxes & fees

9.2/10 Wonderful! (1,919 reviews)

"Great experience"

Reviewed on Jul 15, 2026

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $265

CA $316 total

Aug 16 - Aug 17

includes taxes & fees

8/10 Very good! (10,274 reviews)

"Upon arriving at the hotel - some of the doors worked others did not - their signage was very confusing. When we entered our room there was a horrible smell, one of the curtains was falling from the wall. When we tried to take showers there wasn’t any hot water no matter which way you turned the ..."

Reviewed on Jul 16, 2026

See all 1,553 properties in Downtown Chicago

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 does a Downtown Chicago vacation package cost?

Go from looking to booking with our Downtown Chicago vacation packages, which start from just CA $777. Handpick the hotels and flights that suit your travel style. Then, add on a couple of tours or activities for an amazing adventure.

How do I get a cheap travel package to Downtown Chicago?

Bundle your bookings with Expedia to save big on your next trip. With more than 550 partner airlines and 1,000,000 hotels across the world, your Downtown Chicago vacation package can be tailored exactly to suit your budget. With all that extra money, why not include one or two fun tours and activities? It's an easy way to unlock even more savings. The vacation you've always dreamed of in Downtown Chicago is much closer than you thought!

How far in advance should I book my Downtown Chicago vacation?

While not all airlines advertise tickets early, you can normally look up international airfares on Expedia up to 12 months in advance. This is the time you'll score some incredible deals. If you've left things to the last minute, you could still be in luck. Discounted prices occasionally emerge a few weeks before departure.

What does an Expedia Downtown Chicago travel package include?

Packages include flights, hotels and rental cars, but you can mix and match them to create your ideal Downtown Chicago trip. You can also add on fun things like activities and tours once you've made your booking. You're in charge! When you combine your bookings with Expedia, you'll score discounts you won't find elsewhere.

What should I know before booking a Downtown Chicago travel package?

Our prices are always low. However, you'll pick up even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and tons of choice.

Can I choose my airline with a Downtown Chicago Expedia vacation package?

Yes — that's the beauty of an Expedia vacation package. You're in charge! We have more than 550 partner airlines throughout the world, so you have lots of choice when arranging your Downtown Chicago trip.

If I'm not able to travel, can I cancel my Downtown Chicago vacation package?

You can. We understand that even the best-laid plans can go awry, so we're happy to help if you have to make changes to your Downtown Chicago vacation package. You may be able to change or cancel your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.