Search Deals onWoodstock Vacation Packages
Woodstock Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago
Price was $446, price is now $294 per person
$294
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Four Seasons Hotel Chicago
Price was $4,740, price is now $2,744 per person
$2,744
per person
Sep 13 - Sep 19
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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Save 100% on your flight
Price was $997, price is now $619 per person
$619
per person
Oct 18 - Oct 21
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.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $876, price is now $568 per person
$568
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $522, price is now $350 per person
$350
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago - River North
Save 100% on your flight
Price was $3,143, price is now $2,130 per person
$2,130
per person
Sep 13 - Sep 19
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. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The only thing that was negative was it took forever to check in and limited parking by the lobby entrance.
Reviewed on Aug 7, 2026
Eurostars Magnificent Mile
Save 100% on your flight
Price was $1,038, price is now $705 per person
$705
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
Worst hotel stay in Chicago.
Reviewed on Aug 6, 2026
Level Chicago Fulton Market
Save 100% on your flight
Price was $1,070, price is now $733 per person
$733
per person
Oct 18 - Oct 21
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.
Great staff, great place!
Reviewed on Aug 5, 2026
Woodstock Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Woodstock Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Aug 29 - Sat, Sep 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 2 hours ago
$171
Roundtrip
found 2 hours ago
Wed, Nov 4 - Wed, Nov 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 8 hours ago
$197
Roundtrip
found 8 hours ago
Wed, Sep 2 - Tue, Sep 8
LAX
Los Angeles Intl.
RFD
Greater Rockford
$250 Roundtrip, found 3 days ago
$250
Roundtrip
found 3 days ago
Tue, Sep 1 - Fri, Sep 18
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,131 Roundtrip, found 3 days ago
$1,131
Roundtrip
found 3 days ago
Discover Other Travel Deals
- Woodstock Square Vacations
- Bull Valley Golf Club Vacations
- McHenry County Fairgrounds Vacations
- Woodstock Opera House Vacations
- McHenry County Courthouse Vacations
- Woodstock City Hall Vacations
- Naturally McHenry County Visitor Center Vacations
- Emricson Park Vacations
- Crystal Woods Golf Club Vacations
- Craig Woods Golf Club Vacations
- Geneva Lake Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
