Gresham Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

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

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

Your Gresham Vacation

Say goodbye to planning hassles and hello to a Gresham vacation package. With the finer details organized before you leave, you can focus on discovering this city, starting with Magnificent Mile, which is good for cafes, shopping and history. Need some sightseeing tips for your trip to Gresham? Carter G. Woodson Library and Highland Community Bank are two major attractions here. No matter your travel plans or the size of your budget, putting together a tailored Gresham vacation is a cinch with Expedia.

Top Holiday Package Deals in Gresham

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on Jul. 12, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
Hotel staff and room were awesome..bed very comfortable. Coffee shop was great had great fast breakfast options. Had Miss Rickie's one day was really great food. Only complaint would be the rooftop bar evening clientele...did not feel comfortable and they were loud and raucous.

Reviewed on Jul. 8, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Gorgeous room with a breathtaking view!

Reviewed on Jul. 10, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 24 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (627 reviews)
This place was secure and beautiful. The amenities were top notch & I felt 100% safe while there. Will return!

Reviewed on Jul. 7, 2025

Where to stay in Gresham

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

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Gresham 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 $202 per night from Aug 5 to Aug 6
CA $202
CA $238 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,928 reviews)
"Good location.good staff."

Reviewed on Jul. 9, 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
The price is CA $306 per night from Jul 24 to Jul 25
CA $306
CA $403 total
Jul 24 - Jul 25
includes taxes & fees
9/10 Wonderful! (2,011 reviews)
"The bed was a bit soft. And the pillows could use and update"

Reviewed on Jul. 10, 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
The price is CA $206 per night from Aug 10 to Aug 11
CA $206
CA $242 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,425 reviews)
"Great location and rooms are spacious and clean."

Reviewed on Jul. 11, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,444 properties in Gresham
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 Gresham vacation package cost?
The most affordable Gresham package is CA $761, so the trip of your dreams can become a reality --- without breaking the bank. Bundle flights, hotels, car rentals and more to create a package that matches your travel style.
How do I get a cheap travel package to Gresham?
Our Gresham vacation packages mean plenty of savings for the savvy explorer. For the best deal, simply combine your flights, hotels and activities into one neat package. But bargain prices are only the start of your next big adventure. When you book with Expedia, you'll have more than 550 air carriers and 1,000,000 hotel options all over the world to choose from. Whatever your style or budget, there's a vacation package with your name on it.
Where should I stay in Gresham?
With so much to do in Gresham, it's a good idea to secure a room in a hotel close to its attractions. Dr. Percy Julian Residence, Highland Community Bank and Carter G. Woodson Library are some fascinating ones to put on your to-do list.
How far in advance should I book my Gresham vacation?
Travelers can normally browse international airfares on Expedia within 12 months of departure. Booking late? With a bit of luck, it's still possible to purchase a cheap ticket just weeks before your flight.
What does an Expedia Gresham travel package include?
Packages include hotels, flights and rental cars, but you can combine any of them to create your ideal Gresham getaway. You can also add on fun stuff like activities and experiences once you've made your booking. You're in charge! When you bundle your bookings with Expedia, you'll enjoy discounts you won't find anywhere else.
What should I know before booking a Gresham travel package?
Bundling your bookings into a Gresham vacation package is the most convenient way to organize your trip. Not only that, you'll save when you combine your flights, hotels and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a Gresham Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you definitely can. Simply select your preferred carrier and craft your ideal Gresham escape.
If I'm not able to travel, can I cancel my Gresham vacation package?
Don't stress if you're rethinking your Gresham vacation package --- you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We totally get that your circumstances can change suddenly, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.

Things to do

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
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.