Downtown Chicago Vacations from ￥85,664

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The Latest Downtown Chicago Vacation Packages

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

Hilton Chicago

4 out of 5
Downtown Chicago
Price was ￥119,524, price is now ￥85,664 per person
￥85,664
per person
Jun 12 - Jun 14
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,718 reviews)
Always a great stay! Love this hotel. Great area with great restaurants and fun things to do close by.

Reviewed on Apr 11, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥142,282, price is now ￥86,464 per person
￥86,464
per person
Jun 12 - Jun 14
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The place was beautiful. Breakfast was lovely and I enjoyed everything.

Reviewed on Apr 10, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥184,121, price is now ￥127,349 per person
￥127,349
per person
Jun 12 - Jun 14
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!

Reviewed on Apr 7, 2026

Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Save 100% on your flight
Price was ￥197,612, price is now ￥142,674 per person
￥142,674
per person
Jun 12 - Jun 14
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
Noisy under construction, old in need of updating bath products and amenities are horrible. No extra anything, and all in large built in containers anyone can tamper with so I had to buy product for my stay. Had 12 rooms all billed to me and received no receipts for any of them. Billed rooms to those I had already paid for. Just a bad Hilton experience altogether

Reviewed on Apr 3, 2026

Hilton Garden Inn Chicago Downtown Riverwalk

Hilton Garden Inn Chicago Downtown Riverwalk

3 out of 5
Downtown Chicago
Price was ￥134,050, price is now ￥97,096 per person
￥97,096
per person
Jun 12 - Jun 14
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,874 reviews)
Clean, quiet, comfortable. Very nice stay.

Reviewed on Apr 10, 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
Magnificent Mile

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 ￥19,638 per night from Apr 26 to Apr 27
￥19,638
￥23,054 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,081 reviews)
Good in general

Reviewed on Apr 11, 2026

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 ￥21,833 per night from Apr 26 to Apr 27
￥21,833
￥25,629 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,100 reviews)
Recommend packing light if you self-park and walk to the hotel!

Reviewed on Apr 11, 2026

Hilton Chicago/Magnificent Mile Suites
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 ￥24,763 per night from Apr 19 to Apr 20
￥24,763
￥29,070 total
Apr 19 - Apr 20
includes taxes & fees
8.6/10 Excellent! (5,833 reviews)
Perfect location for a family trip, the hotel amenities were amazing and the staff was very friendly. We did have an issue with having our room serviced during our stay, after a long day out we came back to it still not being serviced, after asking the front desk they said they would put in the request ...

Reviewed on Apr 9, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 1,686 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 ￥85,664. 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

Navy Pier

4.5/5(4,923 reviews)

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

Navy Pier
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(336 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.

Michigan Avenue
Millennium Park

Millennium Park

4.5/5(7,307 reviews)

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

Millennium Park

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,285
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,348
per adult
94% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,427
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.