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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $986, price is now $602 per person
$602
per person
Nov 20 - Nov 22
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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,059, price is now $604 per person
$604
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,211, price is now $741 per person
$741
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,816, price is now $1,165 per person
$1,165
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and babysitting. Enjoy the gym and perks like free WiFi.
Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,051, price is now $694 per person
$694
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The hotel's indoor pool, 24-hour gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and valet parking. A restaurant, laundry facilities, and concierge services are also provided.

Top Darien hotels deals

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
$186 nightly
The price is $221 total per night
$221 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.
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
$155 nightly
The price is $184 total per night
$184 total
Oct 25 - Oct 26
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
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$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.
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
$199 nightly
The price is $237 total per night
$237 total
Oct 1 - Oct 2
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.
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave Chicago IL
$284 nightly
The price is $337 total per night
$337 total
Oct 30 - Oct 31
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.
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
$271 nightly
The price is $322 total per night
$322 total
Oct 29 - Oct 30
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. WiFi in public areas, luggage storage, and concierge services are also on offer.
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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 $602. 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.