Downtown Chicago Vacations from ₩609,938

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The Latest Downtown Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Aug 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8.4/10 Very Good! (3,506 reviews)
Close to Michigan Ave and lots of restaurants. Didn't like that the cleaning lady came at 5pm while we were trying to get ready for dinner. So we didn't get service. Asked the front desk for some coffee creamer to be sent to our room, never received. Beds not the most comfortable.

Reviewed on Jul 29, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Aug 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
The hotel is in a fantastic location. Staff service was very high quality and the lobby and common areas were very clean and well organized. Gym was modern, big and clean. The actual room had some marks on the walls and a buzzy air handling vent in the master. An automated lighting system that was a bit dim and difficult to use. We would stay again. Mini bar and snacks were high quality. We would stay again.

Reviewed on Jul 29, 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Aug 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8.6/10 Excellent! (1,795 reviews)
We recently stayed at the Fairmont Chicago Millennium Park in a Gold Level room for 2 nights and overall had a very good experience. The room was clean, well-sized, and the bed was very comfortable. Water pressure in the shower was excellent—something we definitely appreciate after a long day of walking around the city. The Gold Level service was a highlight. The lounge was well maintained, and the Gold team did a fantastic job keeping the space clean, welcoming, and comfortable. Breakfast, evening canapés, and desserts were enjoyable, though the selection seemed more limited compared to other Fairmont properties we've stayed at. One minor issue: there was no complimentary water in the room upon check-in, but once we called down, it was promptly delivered with no hassle. They had Evian water bottle and other minibar items available but it comes with extra cost. The location is another strong point. It’s about a 10-minute walk to cross the river to Michigan Avenue, 15–20 minutes to Navy Pier, and just 10 minutes to Cloud Gate (The Bean). We didn’t have a car, so we can’t speak to the parking situation. While it didn’t quite match the level of service and amenities we've come to expect from other Fairmont hotels, it was still a comfortable and pleasant stay overall.

Reviewed on Jul 28, 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Aug 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
Todo muy lindo , el personal muy atento, amable la comida exquisita la atención excelente cuando vuelva a Chicago me quedaré de nuevo hay 🙏

Reviewed on Jul 30, 2025

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Aug 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8.8/10 Excellent! (3,033 reviews)
Lots of great dining options around the area. The breakfast at the hotel was great.

Reviewed on Jul 29, 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

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 ₩186,697 per night from Aug 18 to Aug 19
₩186,697
₩219,162 total
Aug 18 - Aug 19
includes taxes & fees
7.8/10 Good! (9,030 reviews)
"There are areas of the property outside that need some tlc. The hallways are outdated in decor but the room was clean and comfortable. The reception area was very pretty. The staff was courteous and friendly. The hotel itself has a good location walkable to the Soldier Field which we were in town ..."

Reviewed on Jul 29, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is ₩318,285 per night from Aug 17 to Aug 18
₩318,285
₩418,109 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (2,137 reviews)
"Elevator"

Reviewed on Jul 28, 2025

InterContinental Chicago Magnificent Mile by IHG
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 ₩199,658 per night from Aug 17 to Aug 18
₩199,658
₩234,378 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (2,535 reviews)
"Staff were friendly. Bell attendants were accommodating and helpful! Facilities were clean and tidy. I would definitely stay there again!"

Reviewed on Jul 29, 2025

Hilton Chicago/Magnificent Mile Suites
See all 1,699 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 ₩609,938. 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

4.5/5(4,870 reviews)

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

4.5/5(7,198 reviews)

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

4.5/5(3,318 reviews)

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.