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Lakeside Vacation Packages

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Lakeside Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $647, price is now $407 per person
$407
per person
Jun 30 - Jul 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $715, price is now $449 per person
$449
per person
Jun 30 - Jul 3
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $682, price is now $430 per person
$430
per person
Jun 30 - Jul 3
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.
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 $1,302, price is now $840 per person
$840
per person
Jun 26 - Jun 29
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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $995, price is now $648 per person
$648
per person
Aug 6 - Aug 9
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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $875, price is now $575 per person
$575
per person
Jul 1 - Jul 5
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 parking (surcharge). 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
Price was $1,320, price is now $883 per person
$883
per person
Jun 30 - Jul 3
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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $947, price is now $635 per person
$635
per person
Aug 6 - Aug 9
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.

Lakeside Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $647, price is now $407 per person
$407
per person
Jun 30 - Jul 3
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 $715, price is now $449 per person
$449
per person
Jun 30 - Jul 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
Save 100% on your flight
Price was $682, price is now $430 per person
$430
per person
Jun 30 - Jul 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,302, price is now $840 per person
$840
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Lakeside Vacation Packages 5-7 Night Stays

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

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,349, price is now $734 per person
$734
per person
Jul 23 - Jul 28
found 17 hours 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 $1,525, price is now $849 per person
$849
per person
Jul 23 - Jul 28
found 17 hours 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 $1,533, price is now $908 per person
$908
per person
Jul 23 - Jul 28
found 17 hours 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 $1,220, price is now $762 per person
$762
per person
Jun 24 - Jun 30
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.

American Airlines
Tue, Oct 20 - Tue, Oct 27
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$219 Roundtrip, just found
$219
Roundtrip
just found
Select American Airlines flight, departing Tue, Oct 20 from Los Angeles Intl. to O'Hare Intl., returning Tue, Oct 27, priced at $219 just found
Delta
Wed, Jul 22 - Wed, Jul 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jul 22 from Los Angeles Intl. to Midway Intl., returning Wed, Jul 29, priced at $239 found 1 day ago
United
Wed, Nov 4 - Mon, Nov 9
LAX
Los Angeles Intl.
SBN
South Bend Intl.
$349 Roundtrip, found 5 hours ago
$349
Roundtrip
found 5 hours ago
Select United flight, departing Wed, Nov 4 from Los Angeles Intl. to South Bend Intl., returning Mon, Nov 9, priced at $349 found 5 hours ago
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$418 Roundtrip, found 1 day ago
$418
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $418 found 1 day ago