Hooppole Vacations

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Hooppole Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was $695, price is now $529 per person
$529
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Omaha (OMA) 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 Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,306, price is now $858 per person
$858
per person
Dec 24 - 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 breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $981, price is now $731 per person
$731
per person
Dec 24 - 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 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.
Very beautiful room with great view... no complaints

Reviewed on Nov 1, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was $728, price is now $555 per person
$555
per person
Dec 24 - 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 breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $841, price is now $642 per person
$642
per person
Dec 24 - 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, 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

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $788, price is now $616 per person
$616
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
very loud. at night = motorcycles outside all night. inside, drunk people screaming and pounding doors = was awakened two days in a row btw 330 and 5 am by loud guests. to their credit, the front desk called security. the smell of marijuana was not uncommon in the hallways. it was a good location for the event we were attending but this is second tier hotel w/ very well meaning staff.

Reviewed on Nov 3, 2026

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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.

United
Sun, Nov 15 - Sat, Nov 21
DEN
Denver Intl.
MLI
Quad City Intl.
$369 Roundtrip, found 3 days ago
$369
Roundtrip
found 3 days ago
Select United flight, departing Sun, Nov 15 from Denver Intl. to Quad City Intl., returning Sat, Nov 21, priced at $369 found 3 days ago
Delta
Tue, Nov 17 - Fri, Dec 4
DEN
Denver Intl.
MLI
Quad City Intl.
$379 Roundtrip, found 3 days ago
$379
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Nov 17 from Denver Intl. to Quad City Intl., returning Fri, Dec 4, priced at $379 found 3 days ago
American Airlines
Sun, Nov 15 - Sat, Nov 21
DEN
Denver Intl.
MLI
Quad City Intl.
$379 Roundtrip, found 3 days ago
$379
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, Nov 15 from Denver Intl. to Quad City Intl., returning Sat, Nov 21, priced at $379 found 3 days ago
Delta
Sat, Nov 21 - Fri, Dec 4
DEN
Denver Intl.
MLI
Quad City Intl.
$399 Roundtrip, found 3 days ago
$399
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Nov 21 from Denver Intl. to Quad City Intl., returning Fri, Dec 4, priced at $399 found 3 days ago