Search Deals onOrland Square Vacation Packages
Orland Square Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Lodge Geneva National
Save 100% on your flight
Price was $381, price is now $244 per person
$244
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this golf resort in Lake Geneva. Enjoy an outdoor pool, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant in our reviews. Popular attractions Geneva Lake and Geneva National Golf Club are located nearby.
The Emily Hotel
Price was $1,509, price is now $776 per person
$776
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.
Level Chicago – Old Town
Save 100% on your flight
Price was $1,271, price is now $659 per person
$659
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The French Country Inn Lake Geneva
Save 100% on your flight
Price was $500, price is now $293 per person
$293
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Lake Geneva. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Geneva National Golf Club and Lake Como are located nearby.
Destination Geneva National
Save 100% on your flight
Price was $415, price is now $250 per person
$250
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this golf hotel in Lake Geneva. Enjoy free parking, an outdoor pool, and 5 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Geneva National Golf Club and Kishwauketoe Nature Conservancy are located nearby.
Level Chicago - River North
Save 100% on your flight
Price was $1,264, price is now $776 per person
$776
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $878, price is now $551 per person
$551
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) 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.
Holiday Inn Club Vacations at Lake Geneva Resort by IHG
Save 100% on your flight
Price was $452, price is now $290 per person
$290
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa resort in Lake Geneva. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions The Highlands Golf Course and The Brute Golf Course are located nearby.
Sentral Michigan Avenue
Save 100% on your flight
Price was $881, price is now $566 per person
$566
per person
Dec 30 - Jan 3
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Soldier Field and Millennium Park are located nearby.
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Save 100% on your flight
Price was $609, price is now $392 per person
$392
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Save 100% on your flight
Price was $462, price is now $300 per person
$300
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Rosemont Theatre are located nearby.
Eurostars Magnificent Mile
Save 100% on your flight
Price was $688, price is now $457 per person
$457
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
3-4 Night Vacations in Orland Square
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Orland Square
Price found within the past 48 hours. Click for updated prices.
Orland Square Last Minute Hotel Deals
Hampton Inn & Suites Chicago Medical District UIC
710 S Seeley Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions United Center and Chicago ...
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
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 ...
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
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 ...
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
Hilton Garden Inn Chicago Downtown South Loop
55 E 11th Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
Homewood Suites by Hilton Chicago Downtown South Loop
59 E. 11th Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Hilton Chicago
720 S Michigan Ave Chicago IL
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 ...
Best Western Grant Park Hotel
1100 S Michigan Ave Chicago IL
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 ...
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.
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