Book Exclusive Oakbrook Terrace Vacation Packages

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Oakbrook Terrace flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $801, price is now CA $575 per person
CA $575
per person
Feb 13 - Feb 16
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,127, price is now CA $704 per person
CA $704
per person
Mar 5 - Mar 10
found 4 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was CA $1,262, price is now CA $858 per person
CA $858
per person
Mar 5 - Mar 10
found 4 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Soldier Field are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,003, price is now CA $1,375 per person
CA $1,375
per person
Feb 14 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $2,389, price is now CA $1,761 per person
CA $1,761
per person
Feb 14 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Top Oakbrook Terrace hotels deals

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $175 per night
CA $175
CA $240 total
Dec 27 - Dec 28
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Pool
Spa
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $123 per night
CA $123
CA $145 total
Jan 5 - Jan 6, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pet-friendly
Free WiFi
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Free cancellation
Reserve now, pay when you stay
Get rates
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Free WiFi
Air conditioning
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Get rates
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pet-friendly
Free WiFi
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $157 per night
CA $157
CA $225 total
Dec 27 - Dec 28
includes taxes & fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Soldier Field are located nearby.
Pool
Hot tub
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $133 per night
CA $133
CA $156 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Spa
Free WiFi
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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.

Popular places to visit

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

Michigan Avenue

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

Wrigley Field

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Wrigley Field
McCormick Place

McCormick Place

During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed theater scene and notable monuments in this vibrant area.

McCormick Place

Oakbrook Terrace Vacations

Get your trip started on the right foot by familiarizing yourself with Oakbrook Terrace before you jet off.

A neighborhood in the popular city of Chicago, Oakbrook Terrace is 18 miles (29 kilometers) west of the heart of the action.

At last count, the population of Chicago was 2,700,000.

Places to visit in Oakbrook Terrace

Get together with like-minded peers and get prepared to be inspired at one of the conferences or events hosted at Drury Lane Theater. Need some more options? Oakbrook Center Mall is the perfect place to go if you feel like a bit of window-shopping. With crowds of people coming and going, you'll have stacks of fellow shopaholics to keep you company!

Where do you fly into for Oakbrook Terrace?

Pack your bags, grab your passport and prepare for a wild adventure. When you touch down at O'Hare International Airport (ORD), you'll be just 9 miles (14 kilometers) to the north of Oakbrook Terrace.

Frequently asked questions

How much are vacation packages to Oakbrook Terrace?
With vacation packages being sold for only CA $575, there's no need to empty your piggy bank to travel to Oakbrook Terrace. Travelocity can help. Combine experiences, flights and hotels into a package and score some impressive discounts. The more you book, the bigger the savings.
How long should my Oakbrook Terrace vacation be?
Most travelers book their hotel for 2 nights in Oakbrook Terrace. But that doesn't necessarily mean you have to do that. How long you stay all depends on what you feel like doing on your vacation. If you intend to explore every inch of this fantastic place, consider staying another night or so (or even an extra week!).
Where can I get the best vacation package deals for Oakbrook Terrace?
For an affordable package deal to Oakbrook Terrace, you can't go past Travelocity. Take your pick of 400 partner airlines and 1,000,000 properties across the globe to create your dream trip — it's as easy as that.
Why should I book my Oakbrook Terrace vacation package via Travelocity?
With exceptional service, customer support available 24/7 and some of the most idyllic getaways money can buy, you'll never roam alone. And if you happen to find a better price, we'll match it. That's our Price Match Guarantee.
Can I save money on my Oakbrook Terrace car rental if I combine it with a hotel or flight?
Bundling your car, flight and hotel into an Oakbrook Terrace vacation package is an easy way to score an incredible deal. Plus, having your own wheels gives you total freedom to find your way to all those big-name sights you're itching to check out. Located 56 kilometers from Oakbrook Terrace, Six Flags Great America is one attraction that should be on your agenda. Put together a driving playlist and make a day trip of it.
Which airport is best for Oakbrook Terrace?
O'Hare Intl. Airport (ORD) is one of the busiest airports in Oakbrook Terrace. It's roughly 14 kilometers north of the city center. Your other options are Midway Intl. Airport (MDW) (21 kilometers away from central Oakbrook Terrace) and Lewis University Airport (LOT) (29 kilometers away from central Oakbrook Terrace).
Where should I stay when visiting Oakbrook Terrace?
Many travelers hit the hay at the Sleep Inn Oakbrook Terrace - Chicago. It's sure to be a great base for your Oakbrook Terrace escape.

Photos of local treasures

Browse Oakbrook Terrace vacation photos for more inspiration