Portage Park 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.
  • Seasonal outdoor pool, sun loungers
    Aug 7 - Aug 10

    Hilton Grand Vacations Club Chicago Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    3.5 star property
    9.2/10 - Wonderful (394 reviews)
    "The room was very nice and smelled very nice."
    Reviewed May 8, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,339
    CA $964
    per traveller
    found 1 day ago
    Hilton Grand Vacations Club Chicago Magnificent Mile
  • Full-size fridge, microwave, oven, stovetop
    Aug 2 - Aug 7

    Level Chicago – Old Town + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.0/10 - Wonderful (480 reviews)
    "Super nice"
    Reviewed May 20, 2026
    Roundtrip • Hamilton (YHM) - Chicago (ORD)
    YHM - ORD • 1 stop ORD - YYZ • 1 stop
    CA $2,232
    CA $1,411
    per traveller
    found 11 hours ago
    Level Chicago – Old Town
  • Smart TV
    Jun 27 - Jul 1

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (487 reviews)
    "Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."
    Reviewed May 22, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YKF • Nonstop
    CA $1,498
    CA $980
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Premium bedding, pillowtop beds, in-room safe, individually furnished
    Aug 2 - Aug 7

    Level Chicago - River North + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,007 reviews)
    "I’ve stayed at this property a few times now and each time they make sure everything is ok. I’ve had little hiccups with the stay but they always make it right., Each time I’m in the area I will be staying with them the location is great and not to busy."
    Reviewed May 23, 2026
    Roundtrip • Hamilton (YHM) - Chicago (ORD)
    YHM - ORD • 1 stop ORD - YYZ • 1 stop
    CA $2,886
    CA $1,927
    per traveller
    found 11 hours ago
    Level Chicago - River North
  • 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

Where to stay in Portage Park

Find the best Portage Park areas and neighborhoods for the activities you enjoy most. Learn more about Portage Park
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

Portage Park 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 $254 per night from May 27 to May 28
CA $254
CA $342 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (4,219 reviews)
"Great location. Very good breakfast for being included. Very responsive and attentive staff. Could have used more electrical plugs in the room. Would definitely stay here again."

Reviewed on May 24, 2026

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 refundable
The price is CA $178 per night from May 27 to May 28
CA $178
CA $212 total
May 27 - May 28
includes taxes & fees
7.8/10 Good! (1,461 reviews)
"My booking stated The hotel Collection on Superior Ave, Chicago, IL had a microwave, refrigerator and coffee pot in the room. The room did not have a refrigerator nor a coffee pot. Coffee was available on the main floor from 5:30am, which was great. The wallpaper in the bathroom was peeling off around ..."

Reviewed on May 23, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,971 properties in Portage Park
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 Portage Park vacation package cost?
Discover the best of Portage Park from just . Choose from a great selection of flights, hotels and rental cars to suit your travel style. You can score even better deals when you add a few activities or tours to your vacation package.
How do I get a cheap travel package to Portage Park?
You'll save piles of cash if you bundle your flights, car rentals and hotels into a Portage Park vacation package. Sometimes cheap means fewer choices. But not with Expedia. We offer more than 550 air carriers and 1,000,000 properties all over the world, which means you'll always have plenty of options to choose from. Want to save even more? Add some fun activities to your package deal to unlock even more bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Portage Park?
A getaway to Portage Park isn't complete without checking out Six Corners, Walt Disney House and The Gift Theatre. Spend your evenings near these popular sights and make sightseeing simple.
How far in advance should I book my Portage Park vacation?
While prices change from time to time, we generally advise booking your flight as early as possible. Most international airfares become available on Expedia up to 12 months in advance. If you're booking late, you might still be in luck. Cheap tickets to Portage Park sometimes appear just weeks before departure.
What does an Expedia Portage Park travel package include?
You can select from any combination of rental cars, hotels and flights. Once you've made your booking, you can add tours and activities. Want to pick your airfare class? That's also easy to do. The choice is yours when it comes to creating your perfect Portage Park getaway.
What should I know before booking a Portage Park travel package?
You'll land excellent savings when you bundle your hotels, flights and rental cars into a package. Not just that, booking everything in one spot simply makes planning easier. So why waste time or money? Whether you're putting together a fancy romantic getaway or an affordable family break, check out our package deals today.
Can I choose my airline with a Portage Park Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You're the boss! We have more than 550 partner airlines across the globe, so you have lots of choice when creating your Portage Park escape.
If I'm not able to travel, can I cancel my Portage Park vacation package?
You can cancel your Portage Park booking if your plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. You may be able to cancel or change your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

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.