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.
Chicago Club Inn & Suites
Price was $616, price is now $538 per person
$538
per person
Dec 24 - Dec 29
found 17 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
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 in our reviews. Popular attractions Oakbrook Center Mall and Ty Warner Park are located nearby.
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was $847, price is now $704 per person
$704
per person
Dec 24 - Dec 29
found 17 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Once you check in, they're going to tell you that you've been selected as a VIP and what that means is you're selected to do a timeshare presentation. DONT DO IT. They're all so rude, and quite frankly racist. They immediately knew that we're not mindless people who wanted to participate so they became rude and one guy started shaking at us because he was so aggravated that we weren't interested. It was SO weird and such a turn off. Anyway. Choose elsewhere. Also the walls are paper thin. We had to change rooms like 3 times. Kevin was nice though.
Reviewed on Nov 2, 2026
Comfort Inn & Suites Geneva - West Chicago
Price was $678, price is now $581 per person
$581
per person
Dec 24 - Dec 29
found 17 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Geneva. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions American Science & Surplus Store and Fabyan Windmill are located nearby.
The hotel was immaculate and the staff was very nice and helpful.
Reviewed on Nov 2, 2026
Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
Price was $876, price is now $771 per person
$771
per person
Dec 24 - Dec 29
found 17 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this boutique 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 Millennium Park are located nearby.
Wel located hotel. Clean. Helpful staff. Too bad they don't offer breakfast.
Reviewed on Nov 1, 2026
DoubleTree by Hilton Lisle Naperville
Price was $658, price is now $579 per person
$579
per person
Dec 24 - Dec 29
found 17 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
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 the clean rooms in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Arrowhead Golf Club are located nearby.
Lisette is awesome
Reviewed on Nov 2, 2026
Hollywood Casino Aurora
Price was $843, price is now $747 per person
$747
per person
Dec 24 - Dec 29
found 17 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
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 Funway Ultimate Entertainment Center are located nearby.
Top Hotel Deals
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
33.93 km from city center
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
30.71 km from city center
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 ...
The Westin Chicago Lombard
70 Yorktown Center Lombard IL
31.09 km from city center
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 ...
Embassy Suites by Hilton Chicago Lombard Oak Brook
707 E Butterfield Road Lombard IL
31.19 km from city center
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 ...
Sybaris Pool Suites
600 Ogden Ave Downers Grove IL
29.98 km from city center
Stay at this hotel in Downers Grove. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Oakbrook Center Mall and Ty Warner Park are ...
Hilton Chicago/Oak Brook Hills Resort & Conference Center
3500 Midwest Road Oak Brook IL
32.58 km from city center
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. ...
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd Willowbrook IL
32.89 km from city center
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 ...
Hollywood Casino Aurora
2500 N Farnsworth Ave Aurora IL
9.87 km from city center
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 ...
Geneva Motel Inn
100 South Tyler Rd St. Charles IL
21.26 km from city center
Book a stay at this business-friendly hotel in St. Charles. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
33.47 km from city center
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. ...
Hyatt Place Chicago/Lombard/Oak Brook
2340 South Fountain Square Drive Lombard IL
31.62 km from city center
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 ...
DoubleTree by Hilton Lisle Naperville
3003 Corporate West Dr Naperville IL
21.33 km from city center
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 ...
Hotel Arista
2139 City Gate Ln Naperville IL
14.74 km from city center
Book a stay at this luxury hotel in Naperville. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
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.
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Thu, Dec 17 - Fri, Dec 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$240 Roundtrip, found 3 days ago
$240
Roundtrip
found 3 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$331 Roundtrip, found 3 days ago
$331
Roundtrip
found 3 days ago