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Gilberts Vacation Packages

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Gilberts Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $298, price is now $183 per person
$183
per person
Feb 7 - Feb 9
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, 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.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Save 100% on your flight
Price was $325, price is now $187 per person
$187
per person
Feb 7 - Feb 9
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $400, price is now $244 per person
$244
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $348, price is now $214 per person
$214
per person
Feb 7 - Feb 9
found 2 days 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $305, price is now $188 per person
$188
per person
Feb 7 - Feb 9
found 2 days 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $643, price is now $404 per person
$404
per person
Feb 14 - Feb 16
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.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $640, price is now $404 per person
$404
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Save 100% on your flight
Price was $592, price is now $378 per person
$378
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Gilberts Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $400, price is now $244 per person
$244
per person
Jan 23 - Jan 26
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 $488, price is now $307 per person
$307
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $640, price is now $404 per person
$404
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $592, price is now $378 per person
$378
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Gilberts Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $610, price is now $344 per person
$344
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $687, price is now $381 per person
$381
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $868, price is now $483 per person
$483
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $724, price is now $407 per person
$407
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)

Top Flight Deals

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

Spirit Airlines
Tue, Dec 30 - Thu, Jan 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$151 Roundtrip, found 6 days ago
$151
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, Dec 30 from Los Angeles Intl. to O'Hare Intl., returning Thu, Jan 8, priced at $151 found 6 days ago
Frontier Airlines
Sat, Feb 7 - Sun, Feb 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$158 Roundtrip, found 19 hours ago
$158
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, Feb 7 from Los Angeles Intl. to O'Hare Intl., returning Sun, Feb 8, priced at $158 found 19 hours ago
Icelandair
Sat, Dec 13 - Mon, Dec 15
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$750 Roundtrip, found 1 day ago
$750
Roundtrip
found 1 day ago
Select Icelandair flight, departing Sat, Dec 13 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Mon, Dec 15, priced at $750 found 1 day ago
Cathay Pacific
Thu, May 7 - Mon, May 18
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,169 Roundtrip, found 1 day ago
$1,169
Roundtrip
found 1 day ago
Select Cathay Pacific flight, departing Thu, May 7 from Pudong Intl. to O'Hare Intl., returning Mon, May 18, priced at $1,169 found 1 day ago