Search Deals on
Woodstock Vacation Packages

Build your package with 2 more options

Leaving from

Going to

Departing

Returning

Travelers

Room 1

Adults

ChildrenAges 2 to 17

InfantsYounger than 2

Add specific hotel dates

A historic building with a clock tower, statues, and an American flag.

Woodstock
Illinois
United States of America
North America
Hotwire.com

Woodstock Flight + Hotel Packages

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

Level Chicago – Old Town

4 out of 5

Save 100% on your flight

Price was $930, price is now $617 per person

$617

per person

Nov 1 - Nov 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago Fulton Market

4 out of 5

Save 100% on your flight

Price was $1,921, price is now $1,128 per person

$1,128

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Trump International Hotel & Tower Chicago

5 out of 5

Save 100% on your flight

Price was $1,652, price is now $1,076 per person

$1,076

per person

Nov 1 - Nov 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Pablo was amazing and he made my 50th birthday experience amazing . Thank you for the champagne and cake surprise . Super recommended .

Reviewed on Sep 1, 2026

The Emily Hotel

4 out of 5

Save 100% on your flight

Price was $2,302, price is now $1,521 per person

$1,521

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.

Love staying at the Emily! Everyone is always so friendly and helpful and the loft style rooms are super comfortable and spacious. The neighborhood has the best food and coffee of every type within walking distance and many clubs as well including Garcia's and Broken Hearts.

Reviewed on Aug 31, 2026

Hotel Riu Plaza Chicago

4 out of 5

Save 100% on your flight

Price was $1,599, price is now $1,059 per person

$1,059

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip flight included

Albuquerque (ABQ) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Everything was great

Reviewed on Sep 1, 2026

Swissotel - Chicago

4.5 out of 5

Save 100% on your flight

Price was $1,747, price is now $1,160 per person

$1,160

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip flight included

Albuquerque (ABQ) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

The Godfrey Hotel Chicago

4.5 out of 5

Save 100% on your flight

Price was $1,098, price is now $736 per person

$736

per person

Oct 13 - Oct 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

The Godfrey was a good hotel.

Reviewed on Sep 1, 2026

The Talbott, Autograph Collection

4.5 out of 5

Save 100% on your flight

Price was $1,504, price is now $1,029 per person

$1,029

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip flight included

Albuquerque (ABQ) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.