Deals on vacations and trips to Darien

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Darien flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $705, price is now $509 per person
$509
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This smoke-free hotel includes 3 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,134, price is now $758 per person
$758
per person
Feb 3 - Feb 9
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Downtown Chicago
Price was $1,001, price is now $695 per person
$695
per person
Feb 3 - Feb 9
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a lobby fireplace, and express check-in are also offered.
Stay One Chicago

Stay One Chicago

4 out of 5
Downtown Chicago
Price was $1,800, price is now $1,273 per person
$1,273
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
This smoke-free hotel includes 3 restaurants, an indoor pool, and A 24-hour gym. Enjoy the seasonal outdoor pool and perks like free WiFi. You'll appreciate the hot tub, poolside bar, and coffee shop.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $693, price is now $511 per person
$511
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Top Darien hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $127 total per night
$127 total
Nov 22 - Nov 23
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Free WiFi
Restaurant
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $117 total per night
$117 total
Dec 10 - Dec 11
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.
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
$160 nightly
The price is $190 total per night
$190 total
Nov 22 - Nov 23
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.
Pool
Hot Tub
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
172 W Adams St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $165 total per night
$165 total
Nov 22 - Nov 23
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A hair salon, express check-in, and express check-out are also on offer.
Pet friendly
Free WiFi
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
71 E Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$146 nightly
The price is $173 total per night
$173 total
Dec 14 - Dec 15
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, conference space, and valet parking. Luggage storage, concierge services, and wedding services are also on offer.
Pet friendly
Free WiFi
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$161 nightly
The price is $192 total per night
$192 total
Nov 24 - Nov 25
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and a lobby fireplace are also offered.
Pet friendly
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.

Stay near popular Darien attractions

National Shrine of St. Therese

7.4/10 (6 reviews)
You can spend an afternoon exploring the galleries in National Shrine of St. Therese in Darien. Wander the forest and lakeside in this trendy area.
See properties

Frequently asked questions

How much are vacation packages to Darien?
You can land an awesome hotel and flight bundle for as low as $509. With a Travelocity vacation package, a getaway to Darien has never looked so enticing! Save both time and cash and then get a start on packing those bags.
How long should my Darien vacation be?
Most visitors stay in Darien for about 5 nights. But travel is all about discovering hidden gems and creating unforgettable memories — why not stay a couple of more nights so you can do just that?
Where can I get the best vacation package deals for Darien?
Scoring a great package deal to Darien is a cinch with Travelocity. With around 400 airlines and 1,000,000 properties around the world, you won't be short of choice when picking your flights and hotels.
Why should I purchase my Darien vacation package via Travelocity?
We take the hassle out of travel planning. Whether you're after a new destination to explore or want to make sure you get the best deal around, we've got your back. Our 24/7 support, excellent service and Price Match Guarantee mean you can confidently book with Travelocity.
Will I save money on my Darien car rental if I combine it with a hotel or flight?
Combining your car, flight and hotel into a Darien vacation package is an easy way to score an amazing deal. Plus, having your own car rental gives you total freedom to get to all those big sights you want to check out. Situated 45 mi from Darien, Six Flags Great America is one place that should have a place on your itinerary. Fill up the tank and make a day trip of it.
Which airport is best for Darien?
O'Hare Intl. Airport (ORD), around 16 mi north of inner Darien, is likely to be where you'll jet into. Your other choices are Midway Intl. Airport (MDW) (12 mi away from central Darien) and Lewis University Airport (LOT) (12 mi away from central Darien).
Where should I stay when visiting Darien?
The WoodSpring Suites Chicago Darien is the first choice of many visitors. Book as soon as possible to avoid missing out.

Photos of local treasures

Browse Darien vacation photos for more inspiration

A waterfall in a forest with autumn leaves.