Search Deals onGilberts Vacation Packages
Gilberts Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
Save 100% on your flight
Price was $939, price is now $587 per person
$587
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The property is close to Michigan avenue which is the Main Street towards millenium park, boardwalk etc. highly recommend.
Room was clean however the air condition was loud, overall is good.
Reviewed on Aug 20, 2026
Level Chicago – Old Town
Price was $1,309, price is now $684 per person
$684
per person
Oct 28 - Nov 3
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.
Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy
Reviewed on Aug 19, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,563, price is now $873 per person
$873
per person
Oct 2 - Oct 6
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.
Level Chicago Fulton Market
Save 100% on your flight
Price was $1,374, price is now $782 per person
$782
per person
Oct 21 - Oct 25
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.
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.
Reviewed on Aug 17, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,319, price is now $834 per person
$834
per person
Oct 21 - Oct 25
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.
Swissotel - Chicago
Save 100% on your flight
Price was $1,401, price is now $919 per person
$919
per person
Oct 21 - Oct 25
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.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $910, price is now $605 per person
$605
per person
Nov 14 - Nov 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.
A+
Reviewed on Aug 20, 2026
The Emily Hotel
Save 100% on your flight
Price was $1,373, price is now $925 per person
$925
per person
Oct 21 - Oct 25
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.
Lovely place in Westloop, close to everything, quiet, clean and efficient. I would stay there again.
Reviewed on Aug 20, 2026
Gilberts Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Gilberts Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Oct 22 - Mon, Oct 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Sat, Sep 19 - Sat, Sep 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$200 Roundtrip, just found
$200
Roundtrip
just found
Fri, Nov 13 - Mon, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,082 Roundtrip, found 4 days ago
$1,082
Roundtrip
found 4 days ago
Tue, Sep 1 - Fri, Sep 18
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,203 Roundtrip, found 18 hours ago
$1,203
Roundtrip
found 18 hours ago
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