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Ingleside Vacation Packages

Build your package with 2 more options

Ingleside Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $647, price is now $424 per person
$424
per person
Dec 17 - Dec 20
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 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.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,023, price is now $626 per person
$626
per person
Dec 31 - Jan 5
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.
Súper cerca a todas las atracciones de Chicago

Reviewed on Oct 12, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $739, price is now $461 per person
$461
per person
Dec 8 - Dec 12
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.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,217, price is now $761 per person
$761
per person
Dec 31 - Jan 5
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 stay was all good as represented on the site!

Reviewed on Oct 12, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,004, price is now $630 per person
$630
per person
Dec 31 - Jan 5
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.
Great service

Reviewed on Oct 13, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,112, price is now $707 per person
$707
per person
Dec 31 - Jan 5
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, 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.

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 $1,581, price is now $1,028 per person
$1,028
per person
Dec 31 - Jan 5
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.

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,194, price is now $777 per person
$777
per person
Nov 14 - Nov 17
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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Great location

Reviewed on Oct 12, 2026

Ingleside Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $647, price is now $424 per person
$424
per person
Dec 17 - Dec 20
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
Save 100% on your flight
Price was $776, price is now $483 per person
$483
per person
Dec 23 - Dec 27
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 $739, price is now $461 per person
$461
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,194, price is now $777 per person
$777
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Ingleside Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $946, price is now $590 per person
$590
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,023, price is now $1,152 per person
$1,152
per person
Nov 14 - Nov 21
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,023, price is now $626 per person
$626
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,116, price is now $1,325 per person
$1,325
per person
Nov 14 - Nov 21
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

Top Flight Deals

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

American Airlines
Thu, Nov 12 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 15 hours ago
$197
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Thu, Nov 12 from Los Angeles Intl. to O'Hare Intl., returning Fri, Nov 13, priced at $197 found 15 hours ago
United
Thu, Nov 12 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 15 hours ago
$197
Roundtrip
found 15 hours ago
Select United flight, departing Thu, Nov 12 from Los Angeles Intl. to O'Hare Intl., returning Fri, Nov 13, priced at $197 found 15 hours ago
Delta
Wed, Nov 11 - Sat, Nov 14
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 15 hours ago
$197
Roundtrip
found 15 hours ago
Select Delta flight, departing Wed, Nov 11 from Los Angeles Intl. to O'Hare Intl., returning Sat, Nov 14, priced at $197 found 15 hours ago
Philippine Airlines
Fri, Nov 13 - Wed, Dec 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$998 Roundtrip, found 1 day ago
$998
Roundtrip
found 1 day ago
Select Philippine Airlines flight, departing Fri, Nov 13 from Pudong Intl. to O'Hare Intl., returning Wed, Dec 2, priced at $998 found 1 day ago