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 Saint Clair- Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $952, price is now $591 per person
$591
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Houston (HOU) 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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,018, price is now $609 per person
$609
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Houston (HOU) 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.
Room was clean & hotel staff was very friendly!
Reviewed on Aug 3, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,517, price is now $951 per person
$951
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,661, price is now $1,071 per person
$1,071
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Houston (HOU) 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.
Could not ask for a better location--walking distance to so many attractions. Hotel was beautiful, and the staff was very nice. Buffet breakfast was excellent, and there is a lovely rooftop bar, but no restaurant or room service (but you can order certain foods and pick them up--we did not partake, so can't comment). We enjoyed our stay immensely, and would not hesitate to stay there again.
Reviewed on Aug 3, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,329, price is now $913 per person
$913
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Houston (HOU) 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.
Hotel 55 Chicago Downtown
Downtown Chicago
Save 100% on your flight
Price was $1,012, price is now $751 per person
$751
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Houston (HOU) 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 Michigan Avenue and Chicago Riverwalk are located nearby.
I loved the location and the staff was great. I really enjoyed my stay and I’ll be back .
Reviewed on Aug 3, 2026
Top Hotel Deals
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. ...
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 ...
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 ...
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 ...
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 onsite spa services. Popular attractions Oakbrook Center Mall and Ty Warner Park are ...
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 ...
Motel 6 Naperville, IL
1585 Naperville Wheaton Road Naperville IL
20.04 km from city center
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
28.79 km from city center
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
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. ...
Holiday Inn Chicago Oakbrook by IHG
17 W. 350 22nd Street Oakbrook Terrace IL
33.99 km from city center
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
22.12 km from city center
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 ...
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, Sep 5 - Sun, Sep 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$178 Roundtrip, found 1 day ago
$178
Roundtrip
found 1 day ago
Sun, Sep 13 - Sat, Sep 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 2 hours ago
$237
Roundtrip
found 2 hours ago
Wed, Sep 16 - Sun, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 2 hours ago
$247
Roundtrip
found 2 hours ago
Wed, Sep 16 - Sun, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 2 hours ago
$247
Roundtrip
found 2 hours ago
Tue, Aug 25 - Sat, Aug 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$277 Roundtrip, found 6 days ago
$277
Roundtrip
found 6 days ago