Hermosa Vacations from $498

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Your Hermosa Vacation

Hermosa is beckoning! Whatever type of break you're organizing, you can see and experience more of this neighborhood with a Hermosa vacation package. Kick off your trip to Hermosa by checking out nearby attractions such as Portage Park, Walt Disney House and Six Corners. No matter your travel goals or the size of your budget, booking the ultimate Hermosa vacation is simple with Expedia.

The Latest Hermosa Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $871, price is now $498 per person
$498
per person
Mar 7 - Mar 12
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,102, price is now $613 per person
$613
per person
Mar 7 - Mar 12
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Good for a girls night out where we had access to bars and dining. Pricey for what you get, room was small, beds were comfy. Good for a night out downtown

Reviewed on Dec 29, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,259, price is now $716 per person
$716
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It was like a Ritz Carlton like experience without the Ritz Carlton price tag.

Reviewed on Dec 31, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $928, price is now $543 per person
$543
per person
Mar 7 - Mar 12
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
The only downfall here was the valet parking. They give you a ticket to call ahead but then you get to the front and THEN they have someone go get a car 15+ minutes away. Some days only one kid is working and has multiple cars to get and bring back. Obviously not his fault! But the process needs tweaking and is frustrating. Also, wouldn’t necessarily recommend for a family with small kids. But it did what it needed to for our stay.

Reviewed on Dec 30, 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,257, price is now $755 per person
$755
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Views were great balcony included but bed was uncomfortable

Reviewed on Dec 30, 2025

Where to stay in Hermosa

Find the best Hermosa areas and neighborhoods for the activities you enjoy most. Learn more about Hermosa
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Hermosa Hotel Deals

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $192 total per night from Jan 11 to Jan 12
$192 total
Jan 11 - Jan 12
Total with taxes and fees
8.4/10 Very Good! (2,445 reviews)
Best option for us while attending an event at McCormick place, with ability to park in public parking that is cheaper than the hotel parking!

Reviewed on Dec 30, 2025

Hilton Chicago
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
$89 nightly
The price is $105 total per night from Jan 8 to Jan 9
$105 total
Jan 8 - Jan 9
Total with taxes and fees
8.8/10 Excellent! (3,613 reviews)
Clean room , great location.

Reviewed on Dec 30, 2025

Hilton Chicago/Magnificent Mile Suites
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $192 total per night from Jan 11 to Jan 12
$192 total
Jan 11 - Jan 12
Total with taxes and fees
8.4/10 Very Good! (2,201 reviews)
Easy Peasy. Beautiful hotel at a great price.

Reviewed on Jan 1, 2026

Palmer House a Hilton Hotel
See all 4,956 properties in Hermosa
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Hermosa

Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 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
Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
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

Things to do

River tour boat in Chicago

Architecture River Tour

$44
per adult
96% of travellers recommend
Architecture River Tour
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$83
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.