Oakton Vacations from $437
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Your Oakton Vacation
Book a customized Oakton vacation package that has everything you need and nothing you don't. Good for cafes, nature and bars and pubs, consider staying in the neighborhood of Rogers Park. There's loads to see and do during your trip to Oakton, including Rivers Casino and Arndt Park. Expedia has what you need to escape your daily routine. Tailor your vacation to Oakton to suit your style of travel, whatever that may be.
The Latest Oakton Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $715, price is now $437 per person
$437
per person
Aug 20 - Aug 22
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,391 reviews)
Breakfast, staff, near everything
Reviewed on Jun 14, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,183, price is now $774 per person
$774
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
Modern interior design of the lobby and cleanliness of the room.
Reviewed on Jun 14, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,631, price is now $1,088 per person
$1,088
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.
Reviewed on Jun 14, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,059, price is now $715 per person
$715
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (484 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Hilton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
Price was $935, price is now $637 per person
$637
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,329 reviews)
Welcoming, helpful staff, Clean, quiet room, Lovely, comfortable Hilton bed. Outstanding fitness room with new Life Fitness equipment! Great breakfast and Honors benefits, Just steps to terminal and train service.
Reviewed on Jun 13, 2026
Where to stay in Oakton
Find the best Oakton areas and neighborhoods for the activities you enjoy most. Learn more about Oakton
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Oakton Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $162 total per night from Jun 29 to Jun 30
$162 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,279 reviews)
"It was an awesome location, clean, and vintage, which I really loved. Walking you will have to go north to everything which is no more than a 20 minute walk. I didn’t use the bar so I can’t rate that. I didn’t like that there wasn’t a pool but overall service was great. I would definitely stay again ..."
Reviewed on Jun 15, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
$146 nightly
The price is $174 total per night from Jun 30 to Jul 1
$174 total
Jun 30 - Jul 1
Total with taxes and fees
7.8/10 Good! (1,586 reviews)
"Older property but locations is great! One block from miracle mile. Rooftop bar was great. Staff wonderful! Had a fitness center that I didn’t use but it was quite large with lots of equipment. The breakfast buffet was adequate but not spectacular. The bus stop is one block from hotel and runs frequently ..."
Reviewed on Jun 15, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $154 total per night from Jun 28 to Jun 29
$154 total
Jun 28 - Jun 29
Total with taxes and fees
8.8/10 Excellent! (2,670 reviews)
"The hotel itself is nice staff friendly but beware of parking costs and expensive breakfast buffet. Would stay again."
Reviewed on Jun 14, 2026
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.