Name: Hyatt Regency O'Hare Chicago
Price range: CA $181
Rating: 8.8

Your Darien Vacation

There's tons to love about Darien, from its rich history to its spectacular views. When you're ready to spend some time in this captivating city, our Darien vacation packages will be perfect for you. If your trip to Darien includes some sightseeing, hit up well-known attractions like Morton Arboretum, Promenade Bolingbrook and Cog Hill Golf & Country Club. Whatever your travel plans or budget, organizing a tailored Darien vacation is easy with Expedia.

Top Darien Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

CA $784

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

8.6/10 Excellent! (1,003 reviews)

Clean large room. Friendly helpful staff. Garage parking with covered bridge to hotel and casino. Highly recommend.

Reviewed on Jun 25, 2026

Hotel Felix River North/Magnificent Mile

Downtown Chicago

CA $1,398

per person

Aug 23 - Aug 29

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.2/10 Very good! (2,797 reviews)

The staff was incredible, they went out of their way to assist and resolve immediately with any issues we had. Marina, Terina, Gazelle, Nicky and the engineer were all great, incuding the cleaning staff. Breakfast and coffee and fruit were fantastic. Will definitely recommend to family and friends and visit again, if we come into the city.

Reviewed on Jun 28, 2026

Level Chicago – Old Town

Downtown Chicago

CA $2,438

per person

Sep 12 - Sep 18

found 20 hours ago

Roundtrip non-stop flight included

Montreal (YUL) 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

Level Chicago - River North

Downtown Chicago

CA $1,956

per person

Aug 11 - Aug 15

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.2/10 Wonderful! (1,034 reviews)

Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.

Reviewed on Jun 19, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $1,113

per person

Aug 29 - Sep 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (504 reviews)

Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!

Reviewed on Jun 25, 2026

Ready to book your vacation to Darien?

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Darien Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $194

CA $230 total

Jun 30 - Jul 1

includes taxes & fees

8/10 Very good! (10,156 reviews)

"This hotel hasn’t been updated in decades. The staff do the best they can with a very old hotel that needs a significant investment to be nice."

Reviewed on Jun 28, 2026

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

CA $361

CA $423 total

Jul 4 - Jul 5

includes taxes & fees

8.4/10 Very good! (2,324 reviews)

"Room was clean. Bar and breakfast were just ok."

Reviewed on Jun 28, 2026

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL

Fully refundableReserve now, pay when you stay

CA $181

CA $206 total

Jul 2 - Jul 3

includes taxes & fees

8.8/10 Excellent! (2,748 reviews)

"Awesome place to stay and wine and dine"

Reviewed on Jun 28, 2026

See all 3,920 properties in Darien

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.