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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $516, price is now $342 per person
$342
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $977, price is now $610 per person
$610
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,240, price is now $793 per person
$793
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $849, price is now $549 per person
$549
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Dry cleaning, luggage storage, and wedding services are also on offer.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

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

3.5 out of 5
Save 100% on your flight
Price was $1,049, price is now $694 per person
$694
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, 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
$111 nightly
The price is $132 total per night
$132 total
Nov 2 - Nov 3
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
$161 nightly
The price is $191 total per night
$191 total
Oct 25 - Oct 26
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
$190 nightly
The price is $226 total per night
$226 total
Oct 30 - Oct 31
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
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Free Cancellation
Reserve now, pay when you stay
$204 nightly
The price is $240 total per night
$240 total
Oct 30 - Oct 31
Total with taxes and fees
This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.
Free airport shuttle
Pet friendly
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
$183 nightly
The price is $218 total per night
$218 total
Oct 25 - Oct 26
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
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$178 nightly
The price is $211 total per night
$211 total
Nov 2 - Nov 3
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
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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 $342. 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.