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Orland Square Vacation Packages

Orland Square Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 4 beach bars, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the restaurant and the bar in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Willis Tower and United Center are located nearby.
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a fitness center, and valet parking (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Ambassador Chicago, part of JdV by Hyatt

Ambassador Chicago, part of JdV by Hyatt

4 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 16 hours ago
Roundtrip flight included
Orlando (MCO) 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.
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

3.5 out of 5
Save 100% on your flight
per person
Jul 30 - Aug 6
found 9 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Willis Tower and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the helpful staff 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.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 12 - Jul 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 12 - Jul 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 1 - Aug 5
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 12 - Jul 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)

5-7 Night Vacations in Orland Square

Price found within the past 48 hours. Click for updated prices.
W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 6
found 9 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 6
found 9 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 6
found 9 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 6
found 9 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)

Orland Square Last Minute Hotel Deals

The Champagne Lodge & Luxury Suites
The Champagne Lodge & Luxury Suites
3.5 out of 5
16 W 621 S. Frontage Rd, Willowbrook, IL
Stay at this 3.5-star boutique hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
The Champagne Lodge & Luxury Suites
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. ...
Embassy Suites by Hilton Chicago Downtown River North
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
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 ...
River Hotel
Hotel Chicago West Loop
Hotel Chicago West Loop
2.5 out of 5
1622 W Jackson Blvd, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff ...
Hotel Chicago West Loop
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
Club Quarters Hotel, Central Loop, Chicago
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
Travelodge by Wyndham Downtown Chicago
Best Western Grant Park Hotel
Best Western Grant Park Hotel
2.5 out of 5
1100 S Michigan Ave, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
Best Western Grant Park Hotel
See all 5,083 properties in Orland Square
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.

Book the perfect getaway to Orland Square

With Hotwire, booking your next trip to Chicago is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Orland Square while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Orland Square flight and hotel package for as low as $417.

Living it up in Chicago means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Orland Square, Chicago vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Orland Square for some of the best accommodations and flight deals.

FAQs about cheap Orland Square packages:

How to get cheap vacation deals to Orland Square?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $99.

How much are Orland Square packages?

Vacation packages to Orland Square vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $417.

How to find cheap car rentals near Orland Square?

Hotwire partners with some of the most reliable car rental companies in Chicago to bring you the best car rental deals in Orland Square for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Orland Square now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Orland Square right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

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