Chicago Ridge Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration

    Find the right fit

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

    Rest easy

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

Your Chicago Ridge Vacation

Say bye-bye to the hassle of planning and hello to a Chicago Ridge vacation package. With everything organized before you take off, you can focus on discovering the best of this city, starting with Hyde Park, which is great for history, nature and culture. If your trip to Chicago Ridge includes a little sightseeing, drop by renowned attractions like SeatGeek Stadium, Chicago Ridge Shopping Mall and Trinity Christian College. Your perfect Chicago Ridge vacation is only clicks away. Explore accommodations, flights and more on Expedia for an adventure that's tailored just for you.

Top Chicago Ridge Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,014 reviews)
Convenient to O’Hare, but the free shuttle did not answer our phone call when we were at the airport needing a ride. From the hotel it was very easy to book it via the front desk.

Reviewed on Jul. 6, 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

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
per person
Sep 15 - Sep 18
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
No reviews
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

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! (1,635 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 23 - 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

Ready to book your vacation to Chicago Ridge?

 

Choose your dates

Chicago Ridge 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 $193 per night from Jul 13 to Jul 14
CA $193
CA $227 total
Jul 13 - Jul 14
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 $278 per night from Aug 10 to Aug 11
CA $278
CA $370 total
Aug 10 - Aug 11
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
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Aug 10 to Aug 11
CA $233
CA $273 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,406 reviews)
"Everything !!"

Reviewed on Jul. 8, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,294 properties in Chicago Ridge
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

Discover the most popular places to visit in Chicago Ridge

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4.5/5(459 reviews)

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

Navy Pier
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 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

What to do in Chicago Ridge

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
94% 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 $61
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Chicago Ridge

Frequently asked questions

How much does a Chicago Ridge vacation package cost?
Offering great value package deals from CA $488 on Expedia, you'll be surprised at how little a vacation to Chicago Ridge costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chicago Ridge?
January, February and November are great times to look for cheap Chicago Ridge vacation packages. Travelling in less busy periods means you can usually find better prices on hotels and flights.
How many days is enough for Chicago Ridge?
To fully enjoy a Chicago Ridge vacation, we recommend staying for 2 days. Split your time between visiting Lake Katherine Nature Centre, Resurrection Cemetery & Mausoleums and other major sights, in addition to exploring neighbourhoods like Clearing and Ashburn. If you've got some time to spare, add a day trip to your Chicago Ridge vacation itinerary.
How to find the best Chicago Ridge package deals?
Start your search for a Chicago Ridge package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Chicago Ridge package deal right away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chicago Ridge adventure underway.
Is it cheaper to book a Chicago Ridge vacation as a package?
You can enjoy significant savings on your Chicago Ridge break by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to view the best hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chicago Ridge?
If you have your Chicago Ridge travel dates confirmed, book as soon as you can to grab some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Chicago Ridge?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Chicago Ridge.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to activities and airfares. Your hotel will likely be the biggest expense during your trip to Chicago Ridge.
  3. Determine how many days away: Start by compiling a list of the sights and activities you want to get to in Chicago Ridge. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, book the ideal Chicago Ridge vacation package for you.

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