Chicago Ridge Vacation Packages

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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.
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
Downtown Chicago
Price was CA $1,081, price is now CA $803 per person
CA $803
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,337 reviews)
Amazing room at a reasonable price! Great location and very friendly staff! Thank you to Jock, who made us feel welcome!

Reviewed on Jun 30, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,375, price is now CA $971 per person
CA $971
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Very clean, great location. Every staff member we encountered was just terrific

Reviewed on Jun 30, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,393, price is now CA $1,698 per person
CA $1,698
per person
Sep 1 - Sep 6
found 2 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well

Reviewed on Jun 26, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,146, price is now CA $832 per person
CA $832
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Very unique motif

Reviewed on Jul 1, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,615, price is now CA $1,205 per person
CA $1,205
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Great stay; fabulous location, amazing views and access to so much; friendly staff. Super friendly and accommodating housekeeping! Food/bar service took a long long time, every time..long wait to order…long wait to get drinks…long wait to pay bill. Not enough staff behind the bar.

Reviewed on Jun 30, 2026

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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 $211 per night from Jul 2 to Jul 3
CA $211
CA $251 total
Jul 2 - Jul 3
includes taxes & fees
8/10 Very good! (10,184 reviews)
"This place was really horrible! The shower was cold as hell and the front desk didn't do anything to help. The room was not wiped down properly and I left first thing on the A.M. when I told the front desk about my stay, they did nothing to fix the issue or reimburse me a portion of my money. I came ..."

Reviewed on Jul 1, 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Jul 5 to Jul 6
CA $217
CA $305 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (1,823 reviews)
"Very clean, great location. Every staff member we encountered was just terrific"

Reviewed on Jun 30, 2026

Omni Chicago Hotel
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is CA $226 per night from Jul 20 to Jul 21
CA $226
CA $257 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (2,757 reviews)
"They over charge your card and then can’t tell what the charge is for or make something up. When we got there they gave us a dirty room and we had to call to get out room changed not a upgrade but whatever."

Reviewed on Jun 30, 2026

Hyatt Regency O'Hare Chicago
See all 4,249 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.
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What to do in Chicago Ridge

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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 $803 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.

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