Braidwood Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Braidwood 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 17 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 17 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 17 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.
Every room has a Lake Michigan view!
Reviewed on Jul 29, 2026
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 17 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 17 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 17 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
Wingate by Wyndham - Joliet
101 McDonald Avenue Joliet IL
28.77 km from city center
Book a stay at this business-friendly hotel in Joliet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
151 N Joliet St Joliet IL
31.48 km from city center
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean ...
Red Roof Inn Chicago - Joliet
1750 Mcdonough St Joliet IL
29.25 km from city center
Stay at this hotel in Joliet. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
Best Western Joliet Inn & Suites
4380 Enterprise Drive Joliet IL
28.69 km from city center
Book a stay at this business-friendly hotel in Joliet. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Super 8 by Wyndham Joliet
1806 McDonough St Joliet IL
29.19 km from city center
Stay at this hotel in Joliet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
La Quinta Inn & Suites by Wyndham Shorewood
19715 NE Frontage Rd Joliet IL
29.3 km from city center
Book a stay at this business-friendly hotel in Joliet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Motel 6 Joliet, IL - I-80
1850 McDonough Road Joliet IL
29.14 km from city center
Stay at this motel in Joliet. Enjoy free WiFi, free parking, and room service. Popular attractions Chicagoland Speedway and Route 66 Raceway are located ...
Days Inn & Suites by Wyndham Morris/I-80
80 Hampton Road Morris IL
22.21 km from city center
Book a stay at this business-friendly hotel in Morris. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Baymont by Wyndham Joliet
1730 MCDONOUGH STREET Joliet IL
29.27 km from city center
Book a stay at this business-friendly hotel in Joliet. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chicagoland Speedway and Route ...
Econo Lodge Shorewood
19755 NE Frontage Rd Joliet IL
29.19 km from city center
Stay at this motel in Joliet. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions West Shore Park and Shorewood-Troy Public Library ...
Holiday Inn & Suites - Joliet Southwest by IHG
1471 Rock Creek Blvd Joliet IL
26.25 km from city center
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
TownePlace Suites by Marriott Joliet South
1515 Riverboat Center Dr Joliet IL
26.16 km from city center
Book a stay at this business-friendly hotel in Joliet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Quality Inn Morris I-80
200 Gore Rd Morris IL
22.08 km from city center
Stay at this hotel in Morris. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Echo Bowling Lanes and Grundy County Speedway are located ...
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 20 hours ago
$203
Roundtrip
found 20 hours ago
Thu, Oct 22 - Sun, Oct 25
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 1 hour ago
$247
Roundtrip
found 1 hour ago
Thu, Oct 22 - Sun, Oct 25
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 1 hour ago
$247
Roundtrip
found 1 hour 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