Central Chicago Vacations from ¥335,878

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to ¥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Central Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Trump International Hotel & Tower Chicago
Sable at Navy Pier Chicago, Curio Collection by Hilton
Eurostars Magnificent Mile
The Allegro Royal Sonesta Hotel Chicago Loop

Where to stay in Central Chicago

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

Find the Best Central Chicago Vacation Packages

Central Chicago Hotel Deals

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥22,202 per night from Sep 3 to Sep 4
¥22,202
¥26,063 total
Sep 3 - Sep 4
includes taxes & fees
The Wade
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 ¥28,980 per night from Sep 15 to Sep 16
¥28,980
¥34,020 total
Sep 15 - Sep 16
includes taxes & fees
Congress Plaza Hotel
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
The price is ¥24,739 per night from Sep 3 to Sep 4
¥24,739
¥29,040 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (4,802 reviews)
"Very nice,everything is around.Highly recommend."

Reviewed on Aug 27, 2025

Embassy Suites by Hilton Chicago Downtown River North
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.

Discover the most popular places to visit in Central Chicago

What to do in Central Chicago

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