Riverside Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Riverside 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 19 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 19 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 19 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 19 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
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
17.04 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
17.93 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
16.52 km from city center
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
17.68 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful ...
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
16.62 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
17.9 km from city center
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
River Hotel
75 East Wacker Drive Chicago IL
17.34 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2 Chicago IL
16.38 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
15.42 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
17.76 km from city center
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 ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
18.12 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
15.77 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
16.62 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
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.
Mon, Aug 24 - Wed, Aug 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$203 Roundtrip, found 21 hours ago
$203
Roundtrip
found 21 hours ago
Thu, Oct 22 - Sun, Oct 25
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 2 hours ago
$247
Roundtrip
found 2 hours ago
Thu, Oct 22 - Sun, Oct 25
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 2 hours ago
$247
Roundtrip
found 2 hours ago
Sat, Sep 5 - Tue, Sep 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 5 days ago
$247
Roundtrip
found 5 days ago
Wed, Sep 2 - Sat, Sep 5
LAX
Los Angeles Intl.
MDW
Midway Intl.
$247 Roundtrip, found 5 days ago
$247
Roundtrip
found 5 days ago