Search Deals onSycamore Vacation Packages
Sycamore Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Save 100% on your flight
Price was $881, price is now $548 per person
$548
per person
Nov 5 - Nov 8
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.
Four Seasons Hotel Chicago
Save 100% on your flight
Price was $1,959, price is now $1,137 per person
$1,137
per person
Nov 5 - Nov 8
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.
Perfect location for shopping, beach, and restaurants. Very clean and staff is very friendly… did not disappoint. Everything met the mark and expectations of a Four Seasons.
Reviewed on Sep 2, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,197, price is now $711 per person
$711
per person
Oct 23 - Oct 27
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 $1,088, price is now $660 per person
$660
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Loved the hotel, super nice and clean! Felt like home away from home!
Reviewed on Sep 1, 2026
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,720, price is now $1,058 per person
$1,058
per person
Nov 20 - Nov 24
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.
The Trump Hotel In Chicago is one of my family's FAVORITE hotels in the world. We stay at The Trump every single time we're in Chicago. It's the BEST.😀👍
Reviewed on Sep 2, 2026
Level Chicago - River North
Save 100% on your flight
Price was $1,106, price is now $733 per person
$733
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Great front desk service and amenities.
Reviewed on Sep 3, 2026
Renaissance Chicago Downtown Hotel
Save 100% on your flight
Price was $905, price is now $615 per person
$615
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Good!
Reviewed on Sep 3, 2026
Swissotel - Chicago
Save 100% on your flight
Price was $1,360, price is now $938 per person
$938
per person
Oct 15 - Oct 18
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 experience! The place was clean, convenient, and comfortable. The staff was friendly and helpful. I would definitely recommend it to other travelers.
Reviewed on Sep 3, 2026
Sycamore Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Sycamore 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, Sep 10 - Sun, Sep 13
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$437 Roundtrip, found 21 hours ago
$437
Roundtrip
found 21 hours ago
Thu, Sep 10 - Sun, Sep 13
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$460 Roundtrip, found 1 day ago
$460
Roundtrip
found 1 day ago
Thu, Sep 10 - Sun, Sep 13
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$519 Roundtrip, found 21 hours ago
$519
Roundtrip
found 21 hours ago
Thu, Sep 10 - Sun, Sep 13
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$530 Roundtrip, found 1 day ago
$530
Roundtrip
found 1 day ago
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