Downtown Chicago Vacations from $345

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Your Downtown Chicago Vacation

Reserving a Downtown Chicago vacation package is a great way to get to know this unique neighborhood. From its must-visit places to its lesser-known delights, you'll be sure to uncover something new. Some leading nearby attractions to see during your trip to Downtown Chicago include Millennium Park, Willis Tower and Art Institute of Chicago. Whatever your travel plans or the size of your budget, booking your dream Downtown Chicago vacation is a cinch with Expedia.

The Latest Downtown Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
Hyatt House Chicago Medical/University District
Hotel Riu Plaza Chicago
LondonHouse Chicago, Curio Collection by Hilton
Arlo Chicago

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

Downtown Chicago Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
$162 nightly
The price is $190 total per night from Jul 13 to Jul 14
$190 total
Jul 13 - Jul 14
Total includes taxes and fees
7.8/10 Good! (8,887 reviews)
"Everything was great loved the lication"

Reviewed on Jul 6, 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
$243 nightly
The price is $280 total per night from Aug 7 to Aug 8
$280 total
Aug 7 - Aug 8
Total includes taxes and fees
9/10 Wonderful! (1,998 reviews)
"The property is next to most restaurants, shopping mall and walking distance to Navy Pier"

Reviewed on Jul 7, 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
$186 nightly
The price is $218 total per night from Jul 10 to Jul 11
$218 total
Jul 10 - Jul 11
Total includes taxes and fees
8.8/10 Excellent! (2,406 reviews)
"Excellent location. Only one block away from the lake as well as from the Michigan avenue (shopping area). Our room was nice and clean. I should not say room, it was like an one bedroom apartment without a kitchen. The management was very nice."

Reviewed on Jul 8, 2025

Hilton Chicago/Magnificent Mile Suites
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 Downtown Chicago

Things to do

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