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.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
$430
per person
Oct 22 - Oct 26
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Where to start…. 1. The “free” breakfast was absolutely awful. Some really big bowls full of cereal, some fruit and a lot of bread. Honestly, one of the worst breakfast buffet I have ever seen. 2. The AC went out in our room and it was over 87° all night. Horrible night sleep. They couldn’t help until the next morning. Yes, they gave us a new room… but why couldn’t they do that overnight. Location was great, but that’s the only plus.
Reviewed on Aug 12, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$777
per person
Oct 22 - Oct 26
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Swissotel - Chicago
Downtown Chicago
$805
per person
Oct 22 - Oct 26
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
$554
per person
Oct 22 - Oct 26
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Great service
Reviewed on Aug 11, 2026
The Talbott, Autograph Collection
Downtown Chicago
$609
per person
Oct 22 - Oct 26
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
$753
per person
Oct 22 - Oct 26
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Great
Reviewed on Aug 12, 2026
Top Hotel Deals
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. ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
Motel 6 Naperville, IL
1585 Naperville Wheaton Road Naperville IL
Stay at this motel 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. ...
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 ...
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. ...
Holiday Inn Chicago Oakbrook by IHG
17 W. 350 22nd Street Oakbrook Terrace IL
Book a stay at this business-friendly hotel in Villa Park. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the clean rooms in our ...
Hampton Inn Joliet-Plainfield I-55
3555 Mall Loop Drive Joliet IL
Stay at this hotel in Joliet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
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.
Thu, Aug 13 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$176
Roundtrip
found 1 day ago
Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$195
Roundtrip
found 7 hours ago
Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$195
Roundtrip
found 7 hours ago
Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$195
Roundtrip
found 7 hours ago
Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$313
Roundtrip
found 7 hours ago
Best points of interest in Montgomery
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