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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $843, price is now $573 per person
$573
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,584, price is now $982 per person
$982
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $954, price is now $599 per person
$599
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $902, price is now $592 per person
$592
per person
Jan 2 - Jan 7
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $951, price is now $660 per person
$660
per person
Jan 2 - Jan 7
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

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
$106 nightly
The price is $126 total per night
$126 total
Nov 10 - Nov 11
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
$116 nightly
The price is $138 total per night
$138 total
Nov 22 - Nov 23
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
$162 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
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$154 nightly
The price is $183 total per night
$183 total
Nov 3 - Nov 4
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also offered.
Pet friendly
Free WiFi
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Free Cancellation
$116 nightly
The price is $138 total per night
$138 total
Nov 22 - Nov 23
Total with taxes and fees
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A snack bar/deli, 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
$186 nightly
The price is $221 total per night
$221 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 business center, conference space, and valet parking. Luggage storage, concierge services, and wedding services are also on offer.
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 $573. 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.