Montclare Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Montclare Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago Downtown
Downtown Chicago
Price was $439, price is now $316 per person
$316
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $604, price is now $415 per person
$415
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,187, price is now $831 per person
$831
per person
Dec 26 - Dec 29
found 18 hours ago
Roundtrip flight included
New York (LGA) 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.
Pendry Chicago
Downtown Chicago
Price was $608, price is now $445 per person
$445
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was $527, price is now $400 per person
$400
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was $521, price is now $405 per person
$405
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
Top Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
14.62 km from Montclare
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
14.92 km from Montclare
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
citizenM Chicago Downtown
80 East Wacker Place Chicago IL
15.06 km from Montclare
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
Warwick Allerton - Chicago
701 North Michigan Avenue Chicago IL
14.88 km from Montclare
Stay at this 4-star family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
14.98 km from Montclare
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl Chicago IL
14.64 km from Montclare
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
15.57 km from Montclare
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave Chicago IL
15 km from Montclare
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our ...
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
15.13 km from Montclare
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
River Hotel
75 East Wacker Drive Chicago IL
14.98 km from Montclare
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
Hilton Chicago
720 S Michigan Ave Chicago IL
15.66 km from Montclare
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Sable at Navy Pier Chicago, Curio Collection by Hilton
900 E Grand Chicago IL
16.61 km from Montclare
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 ...
Pendry Chicago
230 North Michigan Avenue Chicago IL
15.1 km from Montclare
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
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, Dec 4 - Thu, Dec 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 3 days ago
$73
Roundtrip
found 3 days ago
Wed, Dec 3 - Tue, Dec 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 3 days ago
$118
Roundtrip
found 3 days ago
Fri, Dec 5 - Sun, Dec 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$234 Roundtrip, found 7 hours ago
$234
Roundtrip
found 7 hours ago
Fri, Dec 5 - Sun, Dec 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$234 Roundtrip, found 7 hours ago
$234
Roundtrip
found 7 hours ago
Fri, Dec 5 - Sun, Dec 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$263 Roundtrip, found 7 hours ago
$263
Roundtrip
found 7 hours ago