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Hooppole Vacation Packages

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Hooppole Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
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
Price was $1,041, price is now $687 per person
$687
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Save 100% on your flight
Price was $4,896, price is now $2,951 per person
$2,951
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The

Reviewed on Aug 10, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,342, price is now $819 per person
$819
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Great staff, great place!

Reviewed on Aug 5, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,408, price is now $872 per person
$872
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
This was such a great hotel. It’s in a wonderful neighborhood, and walking distance from the Riverwalk and Michigan Ave. I’m a solo female traveler, and I felt safe and comfortable here. The room was great and the bed was cozy. I would definitely stay here again.

Reviewed on Aug 11, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,157, price is now $723 per person
$723
per person
Oct 21 - Oct 24
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, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The property waa clean and spacious Staff were very nice and helpful. The location was perfect a short walk or drive to alot of places ans the best of all was that A Garrett's popcorn shop waa right across the street!

Reviewed on Aug 11, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,167, price is now $752 per person
$752
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,520, price is now $996 per person
$996
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Save 100% on your flight
Price was $1,839, price is now $1,208 per person
$1,208
per person
Oct 27 - Nov 3
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and room service. Our guests praise the clean rooms in our reviews. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Was promised someone would be available to check-in luggage on 2 separate occasions. That did not happen! If remote management is your thing, this place is fine. Not for me!

Reviewed on Aug 9, 2026

Hooppole Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,157, price is now $723 per person
$723
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,342, price is now $819 per person
$819
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,408, price is now $872 per person
$872
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,167, price is now $752 per person
$752
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Hooppole Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,316, price is now $716 per person
$716
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $1,694, price is now $873 per person
$873
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,562, price is now $822 per person
$822
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,348, price is now $727 per person
$727
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Bargain Flight
Sat, Jan 9 - Sat, Jan 23
AUS
Austin-Bergstrom Intl.
MLI
Quad City Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Jan 9 from Austin-Bergstrom Intl. to Quad City Intl., returning Sat, Jan 23, priced at $237 found 1 day ago
Delta
Sat, Jan 23 - Tue, Feb 9
AUS
Austin-Bergstrom Intl.
MLI
Quad City Intl.
$241 Roundtrip, found 1 day ago
$241
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jan 23 from Austin-Bergstrom Intl. to Quad City Intl., returning Tue, Feb 9, priced at $241 found 1 day ago
American Airlines
Sat, Jan 9 - Sat, Jan 23
AUS
Austin-Bergstrom Intl.
MLI
Quad City Intl.
$241 Roundtrip, found 1 day ago
$241
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jan 9 from Austin-Bergstrom Intl. to Quad City Intl., returning Sat, Jan 23, priced at $241 found 1 day ago
United
Sat, Jan 9 - Sat, Jan 23
AUS
Austin-Bergstrom Intl.
MLI
Quad City Intl.
$246 Roundtrip, found 1 day ago
$246
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jan 9 from Austin-Bergstrom Intl. to Quad City Intl., returning Sat, Jan 23, priced at $246 found 1 day ago