Chicago Ridge Holidays
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- Better togetherSave up to S$1,300 when you book a flight and hotel together*
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Chicago Ridge Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
S$701
per person
21 Nov - 27 Nov
found 1 day ago
Return flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (3,105 reviews)
Great place to stay! The location is excellent, close to plenty of restaurants and just one mile from Millennium Park. Subway and bus stations are also nearby, making it easy to get around the city. The staff is very friendly and welcoming. I would definitely recommend this place!
Reviewed on 20 Oct, 2026
Top hotels in Chicago Ridge
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
S$163
10 Nov - 11 Nov
includes taxes & fees
8/10 Very good! (10,177 reviews)
"The room I stayed in 1270 was terrible maintained. It was clean but shower seemed to have be poorly repaired too many times, toilet was loose and a bit crooked, the door nob on the bathroom door coming off, door on the dresser also crooked and tiles on the bathroom floor broken. The hotel does not ..."
Reviewed on 21 Oct, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
S$183
11 Nov - 12 Nov
includes taxes & fees
River Hotel
75 East Wacker Drive Chicago IL
S$232
1 Nov - 2 Nov
includes taxes & fees
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.
What to do in Chicago Ridge
Skydeck Chicago at Willis Tower
S$54
per adult
88% of travellers recommend
Frequently asked questions
How much does a Chicago Ridge holiday package cost?
Offering great value package deals from S$701 on Expedia, you'll be pleasantly surprised at how much a holiday to Chicago Ridge costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chicago Ridge?
If you're hoping to book a cheap Chicago Ridge holiday package, consider planning a trip in January, February and November. You'll generally find better rates on flights and accommodation during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Chicago Ridge?
Usually, a handful of days is enough to visit the major attractions during your Chicago Ridge holiday. However, if you prefer to have time to kick back or go on day tours, think about extending your itinerary.
How to find the best Chicago Ridge package deals?
Begin your search for a Chicago Ridge package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Chicago Ridge package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chicago Ridge adventure off to a flying start.
Is it cheaper to book a Chicago Ridge holiday as a package?
An Expedia holiday package could land you great savings when compared to booking flights and hotels individually. Better still, you can customise your Chicago Ridge escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Chicago Ridge?
If you're planning a spontaneous Chicago Ridge getaway, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Chicago Ridge?
- Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Chicago Ridge.
- Set a budget: Factor in expenses such as flights, meals and transportation when working out how much to save for your trip to Chicago Ridge. Then, choose a property that works with your budget, whether that's a low-cost stay or a deluxe retreat.
- Decide how long to go for: Now that you're more familiar with Chicago Ridge, you can figure out the ideal length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to see.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose a Chicago Ridge holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
