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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $770, price is now $511 per person
$511
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $880, price is now $560 per person
$560
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,176, price is now $749 per person
$749
per person
Nov 14 - Nov 18
found 16 hours ago
Roundtrip flight included
Baltimore (BWI) 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 Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $886, price is now $565 per person
$565
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,403, price is now $898 per person
$898
per person
Nov 26 - Nov 29
found 10 hours ago
Roundtrip flight included
Baltimore (BWI) 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.

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
$179 nightly
The price is $213 total per night
$213 total
Sep 27 - Sep 28
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
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
$188 nightly
The price is $223 total per night
$223 total
Sep 27 - Sep 28
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
Free Cancellation
Reserve now, pay when you stay
$208 nightly
The price is $248 total per night
$248 total
Oct 24 - Oct 25
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
$135 nightly
The price is $161 total per night
$161 total
Sep 27 - Sep 28
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
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
$287 nightly
The price is $341 total per night
$341 total
Sep 27 - Sep 28
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
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$152 nightly
The price is $179 total per night
$179 total
Sep 27 - Sep 28
Total with taxes and fees
This hotel features a restaurant, a coffee shop, and free WiFi in public areas. Express check-out, luggage storage, and free newspapers are also on offer.
Free WiFi
Restaurant
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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 $511. 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.