Shannon Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Shannon Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Save 100% on your flight
Price was $1,584, price is now $1,181 per person
$1,181
per person
Sep 16 - Sep 20
found 18 hours ago
Roundtrip flight included
San Antonio (SAT) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
The hotel had very clean rooms and the staff was friendly and helpful. Breakfast was convenient with good options.
Reviewed on Jul 29, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,554, price is now $1,513 per person
$1,513
per person
Sep 16 - Sep 20
found 18 hours ago
Roundtrip flight included
San Antonio (SAT) 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.
Loved the breakfast. The room was nice and clean. However there are very little amenities here like no ice machines. No grab and go. No pool. My room got hot a few times but hotel maintenance was quick to respond. Other staff members appeared confused when asked a question about amenities. Check in was confusing as well. Staff had trouble finding reservations as well.
Reviewed on Jul 29, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,958, price is now $1,368 per person
$1,368
per person
Sep 16 - Sep 20
found 18 hours ago
Roundtrip flight included
San Antonio (SAT) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,827, price is now $1,302 per person
$1,302
per person
Sep 16 - Sep 20
found 18 hours ago
Roundtrip flight included
San Antonio (SAT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Thompson Chicago, by Hyatt
Downtown Chicago
Save 100% on your flight
Price was $3,517, price is now $2,543 per person
$2,543
per person
Sep 16 - Sep 20
found 18 hours ago
Roundtrip flight included
San Antonio (SAT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 bars/lounges, and room service. 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
Downtown Chicago
Save 100% on your flight
Price was $1,810, price is now $1,338 per person
$1,338
per person
Sep 16 - Sep 20
found 18 hours ago
Roundtrip flight included
San Antonio (SAT) 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.
Top Hotel Deals
Savanna Inn & Suites
101 Valley View Drive Savanna IL
33.26 km from city center
Book a stay at this business-friendly hotel in Savanna. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
16.44 km from city center
Stay at this hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
City Express By Marriott Freeport
1060 Riverside Dr Freeport IL
20.32 km from city center
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Paddle Wheel Inn
1457 IL Rt 2 North Oregon IL
35.76 km from city center
Book a stay at this business-friendly hotel in Oregon. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
Country Inn & Suites by Radisson, Stockton, IL
200 Dillon Ave Stockton IL
31.41 km from city center
Book a stay at this business-friendly hotel in Stockton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
White Pines Lodge
6712 W Pines Rd. Mount Morris IL
28.91 km from city center
Stay at this hotel in Mount Morris. Enjoy free parking, housekeeping, and a restaurant. Popular attractions White Pines Forest State Park and Dillehay Park are ...
SureStay Hotel by Best Western Thomson
5020 IL Rt 84 Thomson IL
34.13 km from city center
Book a stay at this golf hotel in Thomson. Enjoy free breakfast, free parking, and a golf course. Our guests praise the helpful staff in our reviews. Popular ...
Hampton Inn Freeport
109 S Galena Ave Freeport IL
18.57 km from city center
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free parking, and a 24-hour fitness center. Popular attractions Lincoln-Douglas ...
Super 8 by Wyndham Freeport
1551 Sleezer Home Rd Freeport IL
17.7 km from city center
Stay at this hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Stephenson County Historical Museum and Oscar Taylor Home ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sun, Aug 9 - Fri, Aug 14
LAS
Harry Reid Intl.
RFD
Greater Rockford
$760 Roundtrip, found 5 days ago
$760
Roundtrip
found 5 days ago
Sun, Aug 9 - Fri, Aug 14
LAS
Harry Reid Intl.
RFD
Greater Rockford
$770 Roundtrip, found 4 days ago
$770
Roundtrip
found 4 days ago
Sun, Aug 9 - Fri, Aug 14
LAS
Harry Reid Intl.
RFD
Greater Rockford
$830 Roundtrip, found 1 day ago
$830
Roundtrip
found 1 day ago
Sun, Aug 9 - Fri, Aug 14
LAS
Harry Reid Intl.
RFD
Greater Rockford
$845 Roundtrip, found 5 days ago
$845
Roundtrip
found 5 days ago