Downtown Chicago Vacations from ₩451,146

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The Latest Downtown Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

4 out of 5
Downtown Chicago
Price was ₩560,872, price is now ₩451,146 per person
₩451,146
per person
Dec 23 - Dec 25
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (1,042 reviews)
Extremely clean room with updated features. Perfect location. Very walkable!

Reviewed on Oct 31, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ₩660,671, price is now ₩471,249 per person
₩471,249
per person
Dec 23 - Dec 25
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Room was perfect! Rooftop bar was on point and friendly staff

Reviewed on Nov 4, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was ₩604,508, price is now ₩466,281 per person
₩466,281
per person
Dec 23 - Dec 25
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
Staff was so friendly and helpful. Room was comfortable and clean

Reviewed on Nov 4, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ₩673,062, price is now ₩526,205 per person
₩526,205
per person
Dec 23 - Dec 25
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
Really cool modern space

Reviewed on Nov 4, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was ₩664,317, price is now ₩523,494 per person
₩523,494
per person
Dec 23 - Dec 25
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.

Reviewed on Oct 28, 2025

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
Magnificent Mile - River North

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.

Find hotels in Magnificent Mile

Downtown Chicago Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩168,908 per night from Nov 23 to Nov 24
₩168,908
₩198,281 total
Nov 23 - Nov 24
includes taxes & fees
8.4/10 Very Good! (5,196 reviews)
Excellent experience. Breakfast was great and hotel is at a good location.

Reviewed on Nov 4, 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩294,643 per night from Nov 6 to Nov 7
₩294,643
₩345,881 total
Nov 6 - Nov 7
includes taxes & fees
7.8/10 Good! (9,679 reviews)
I love the classical charm of this hotel. High ceiling rooms, curved walls. The staff are friendly and efficient, even though they were handling guests in for at least two major events. Minor quibbles are the drink was very expensive at the bar, the noise beteeen rooms is loud (we used ear plugs ...

Reviewed on Nov 4, 2025

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩144,694 per night from Nov 17 to Nov 18
₩144,694
₩169,856 total
Nov 17 - Nov 18
includes taxes & fees
8.8/10 Excellent! (3,228 reviews)
Great !

Reviewed on Nov 4, 2025

Hilton Chicago/Magnificent Mile Suites
See all 1,744 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 ₩451,146. 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.

Discover the most popular places to visit in Downtown Chicago

Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.