Hermosa Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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
Price found within the past 48 hours. Click for updated prices.
  • Executive lounge
    Jul 28 - Jul 31

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    8.8/10 - Excellent (2,165 reviews)
    "Amazing staff. Clean rooms!"
    Reviewed May 21, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,344
    CA $940
    per traveller
    found 2 days ago
    Fairmont Chicago at Millennium Park
  • Indoor wedding
    Jul 28 - Jul 31

    Swissotel - Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.0/10 - Wonderful (3,337 reviews)
    "Great location!"
    Reviewed May 23, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,579
    CA $1,040
    per traveller
    found 2 days ago
    Swissotel - Chicago
  • Lounge
    Jul 28 - Jul 31

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,116 reviews)
    "Great staff and perfect place to be in the middle of everything!"
    Reviewed April 27, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,707
    CA $1,146
    per traveller
    found 2 days ago
    Pendry Chicago
  • View from property
    Jun 27 - Jul 1

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (116 reviews)
    "We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from. "
    Reviewed May 17, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YKF • Nonstop
    CA $1,574
    CA $1,063
    per traveller
    found 1 day ago
    The Talbott, Autograph Collection
  • Terrace/patio
    Jul 28 - Jul 31

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,509 reviews)
    "Loved this property !"
    Reviewed May 23, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,502
    CA $1,042
    per traveller
    found 2 days ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton

Where to stay in Hermosa

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

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

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 CA $185 per night from May 25 to May 26
CA $185
CA $219 total
May 25 - May 26
includes taxes & fees
8/10 Very Good! (10,134 reviews)
"Great location. Walkable to all the downtown attractions. Historical hotel with updated rooms. Highly recommend."

Reviewed on May 23, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from May 27 to May 28
CA $220
CA $301 total
May 27 - May 28
includes taxes & fees
Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from May 25 to May 26
CA $168
CA $199 total
May 25 - May 26
includes taxes & fees
7.8/10 Good! (1,459 reviews)
"Great stay!! Love the different vouchers. Well worth it!!"

Reviewed on May 23, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,899 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
Family Vacations
Family Vacations

Frequently asked questions

How much does a Hermosa vacation package cost?
We make it easy to travel the world, with Hermosa vacation packages starting from just . You'll have the flexibility to combine your favorite airlines, hotels and car rental. For the ultimate getaway, why not add some tours and experiences to your itinerary?
How do I get a cheap travel package to Hermosa?
Secure flights that fit your busy schedule, add a hotel room to your booking and watch the savings stack up with a Hermosa vacation package. It's that simple! From flights and hotels to activities and rental cars, Expedia makes traveling on a budget easy. And with more than 550 air carriers and 1,000,000 properties around the world to pick from, you'll never be short of choice.
Where should I stay in Hermosa?
With interesting attractions like Portage Park and Six Corners in this area, look for a hotel situated near them. Walt Disney House is another sight that pulls the crowds.
How far in advance should I book my Hermosa vacation?
While prices change from time to time, we generally advise booking your vacation as soon as possible. Many international airfares are found on Expedia up to a year in advance. If circumstances have left you booking late, you might still be lucky. Cheap journeys to Hermosa sometimes appear just weeks before departure.
What does an Expedia Hermosa travel package include?
Much of that depends on you. You can pick from a range of Hermosa bundles, such as a rental car, hotel and flight. You can also book a flight with a hotel, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like experiences and tours. Whatever your perfect Hermosa break looks like, you'll save!
What should I know before booking a Hermosa travel package?
When you book your flights, hotels and car rentals together, you'll pick up awesome discounts. Whether you're planning an outdoor getaway in a chalet or would rather stay in a comfortable hotel in the city, Expedia can help make it happen.
Can I choose my airline with a Hermosa Expedia vacation package?
Yes, and with over 550 airlines to select from globally, you've got lots of choice. Browse the available options and see which airline suits your budget and needs.
If I'm not able to travel, can I cancel my Hermosa vacation package?
Because we know life can throw you a few curveballs, the answer is yes. For further details, head to our Customer Service Portal. But generally speaking, if you've booked your Hermosa vacation package in the last 24 hours, you may be able to change or cancel it without penalty. Your airline, hotel or car rental company may impose a fee if your booking is older than that.

Discover the most popular places to visit in Hermosa

Wrigley Field

Wrigley Field

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

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

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
per child
98% of travellers recommend
Flyover in Chicago
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.