Woodlawn Vacation Packages

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Flight and hotel packages to Woodlawn

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 19 - Jul 21
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
W Chicago - City Center

W Chicago - City Center

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 30 - Jul 3
Roundtrip flight included
Dallas (DFW) 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 snack bar/deli, and a hair salon are also offered.
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 19 - Jul 22
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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 19 - Jul 21
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.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 19 - Jul 22
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A bar/lounge, a 24-hour front desk, and express check-in are also provided.

Top Woodlawn hotel 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
The price is $159 per night
$159
per night
May 13 - May 14
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.
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $171 per night
$171
per night
May 28 - May 29
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
Parking available
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $180 per night
$180
per night
May 27 - May 28
A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $102 per night
$102
per night
May 12 - May 13
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Valet parking, a business center, and a snack bar/deli are also offered.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $128 per night
$128
per night
May 29 - May 30
This hotel features 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 a communal living room are also offered.
Pet friendly
Parking available
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $142 per night
$142
per night
May 12 - May 13
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.
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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.

Popular places to visit in Woodlawn

Image for Jackson Park

Jackson Park

4/5(7 reviews)

Explore the great outdoors at Jackson Park, a lovely green space in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

Jackson Park
Image for 63rd Street Beach

63rd Street Beach

Why not spend a lazy afternoon at 63rd Street Beach during your trip to Chicago? Wander the beaches and gardens while you're in the area.

63rd Street Beach
Image for Lorado Taft's Midway Studios

Lorado Taft's Midway Studios

You can find out about the history of Chicago with a stop at Lorado Taft's Midway Studios. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

Lorado Taft's Midway Studios

Frequently asked questions

How much are vacation packages to Woodlawn?
Starting from as low as $371, hotel and flight packages are the perfect way to make your vacation budget stretch further. Woodlawn, here you come!
Where can I get the best vacation package deals for Woodlawn?
With at least 400 air carriers and 1,000,000 properties around the world, you can’t go wrong with Travelocity. Browse our extensive range and pick up the best package deal to Woodlawn. Isn’t it great when vacation planning is that easy?
Why should I book my Woodlawn vacation package via Travelocity?
From enticing destinations to one-of-a-kind experiences, we have everything you need to satisfy your travel desires. Our friendly 24/7 customer support will also ensure you’re taken care of during your getaway. And don’t fret if you spot a better price on your reservation, we’ll match it. That’s our Price Match Guarantee.
Can I save on my Woodlawn car rental if I combine it with my hotel or flight?
Booking a Woodlawn vacation package with Travelocity is one of the simplest ways to save you money. You can combine a flight, car and hotel, or any combination of them, and score great discounts. You might also like to throw in some tours and experiences. After you’ve collected the keys to the rental car, head out of the neighborhood and find out what the surrounding area has to offer. About 45 mi from Woodlawn, Six Flags Great America is the ideal road trip.
What is the best time of year to go to Woodlawn?
Visit in and you can spend more money on experiences, rather than your hotel. This is the most affordable month to book your getaway. Prices are at their highest in , so avoid traveling then if you want to save. March, May and August are the high season months in Woodlawn. You’ll need to book beforehand and be prepared to pay premium prices. January, September and December are the least popular months to visit.
What is there to do in Woodlawn?
As you’re ambling around Woodlawn, pay a visit to Jackson Park and 63rd Street Beach. This neighborhood will keep you on your toes.