Montgomery Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Montgomery Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$542
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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.
Check-in and check-out were a breeze. Very clean rooms, spacious bathroom. The room was smaller than expected, but perfect for my solo trip. Convenient location, 15 min walk from the river area, 8 min from the Michigan blvd. Aldi 5 min away, Starbuck 2 min away, Wallgreens 2 min away. Seemed pretty safe at night.
Reviewed on Sep 15, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$875
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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.
Great location. So much to do in walking distance and hotel was great.
Reviewed on Sep 16, 2026
The Emily Hotel
Downtown Chicago
$717
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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.
Comfortable room with a great view and luxuriously soft bed!
Reviewed on Sep 13, 2026
Silversmith Hotel Chicago Downtown
Downtown Chicago
$750
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 Millennium Park and Chicago Riverwalk are located nearby.
Kimpton Gray Hotel by IHG
Downtown Chicago
$869
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Clean room, nice location
Reviewed on Sep 15, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,364
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Fresno (FAT) 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.
Top Hotel Deals
DoubleTree by Hilton Lisle Naperville
3003 Corporate West Dr Naperville IL
Book a stay at this business-friendly hotel in Naperville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Book a stay at this business-friendly hotel in Westmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms ...
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hilton Chicago/Oak Brook Hills Resort & Conference Center
3500 Midwest Road Oak Brook IL
Book a stay at this spa resort in Oak Brook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. ...
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Stay at this hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Embassy Suites by Hilton Chicago Lombard Oak Brook
707 E Butterfield Road Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff ...
The Westin Chicago Lombard
70 Yorktown Center Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy 2 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Hollywood Casino Aurora
2500 N Farnsworth Ave Aurora IL
Book a stay at this spa hotel in Aurora. Enjoy a full-service spa, 9 restaurants, and a 24-hour fitness center. Popular attractions Chicago Premium Outlets and ...
Hyatt Regency Lisle near Naperville
1400 Corporetum Drive Lisle IL
Book a stay at this business-friendly hotel in Lisle. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd Willowbrook IL
Book a stay at this boutique hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
Best Western Chicago - Downers Grove
3010 Finley Rd Downers Grove IL
Book a stay at this business-friendly hotel in Downers Grove. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hyatt Place Chicago/Lombard/Oak Brook
2340 South Fountain Square Drive Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Red Roof Inn PLUS+ Chicago - Naperville
1698 West Diehl Road Naperville IL
Stay at this hotel in Naperville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Sybaris Pool Suites
600 Ogden Ave Downers Grove IL
Stay at this hotel in Downers Grove. Enjoy free WiFi, free parking, and onsite spa services. Popular attractions Oakbrook Center Mall and Ty Warner Park are ...
Best Western Naperville Inn
1617 Naperville Wheaton Rd Naperville IL
Book a stay at this business-friendly hotel in Naperville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast 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.
Sat, Oct 10 - Sat, Oct 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$159
Roundtrip
found 5 days ago
Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$206
Roundtrip
found 7 hours ago
Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$215
Roundtrip
found 7 hours ago
Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216
Roundtrip
found 7 hours ago
Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 7 hours ago
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