Search Deals onSycamore Vacation Packages
Sycamore Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $785, price is now $520 per person
$520
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
We had a wonderful stay! The hotel was very clean, and the staff who checked us in and out were incredibly kind and welcoming. The location was perfect—we were able to walk everywhere we wanted to go, which made our trip so convenient. I would definitely stay here again!
Reviewed on Jul 2, 2026

Lodge Geneva National
Save 100% on your flight
Price was $1,083, price is now $696 per person
$696
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this golf resort in Lake Geneva. Enjoy an outdoor pool, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant in our reviews. Popular attractions Lake Como and Geneva Lake are located nearby.
The Lodge is still under renovations. Our room was missing things like a headboard and bedside tables. The water pressure was weak. The amenities were nice for a family stay. It might be great once it’s all done. I wish we knew before booking.
Reviewed on Jun 27, 2026

Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,152, price is now $751 per person
$751
per person
Sep 3 - Sep 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.
The hotel is perfectly located near major tourist attractions, restaurants, and shops—all within easy walking distance. The rooms are clean, spacious, and equipped with all the essential amenities. The only downside is the lack of on-site parking; guests must park across the street for $55 per day.
Reviewed on Jul 2, 2026

Four Seasons Hotel Chicago
Save 100% on your flight
Price was $2,461, price is now $1,616 per person
$1,616
per person
Sep 14 - Sep 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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
This was our first stay at a Four Seasons — if there was 6 stars for the staff, I'd give it. Upon arrival, we were running late and trying to make an event. The Bellman immediately said he'd arrange transportation for us after we quickly went to the restrooms. We come back down to discover that he was going to drive us in the hotel's car —amazing service! And that's how the entire stay went. Amazing service, clean everything, amenities beyond expectations — it was a splurge, but a well worth one and we'll be back again!
Reviewed on Jul 2, 2026

Level Chicago – Old Town
Save 100% on your flight
Price was $1,193, price is now $788 per person
$788
per person
Sep 14 - Sep 17
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.
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026

Omni Chicago Hotel
Save 100% on your flight
Price was $1,005, price is now $676 per person
$676
per person
Aug 13 - Aug 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, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Room had many little things wrong that added up. Shower pressure was poor on hot water but blasting when cold. Bathroom door didn’t slide all the way close. Light in front entryway didn’t turn off. Makeup mirror light did not work. Dresser drawers were uneven and not smooth to close.
Staff told us about discount at American Girl Doll store but when we went there they ask several managers and we were informed we were given misinformation by the hotel staff.
Reviewed on Jul 2, 2026

Hampton Inn & Suites Chicago Medical District UIC
Save 100% on your flight
Price was $976, price is now $658 per person
$658
per person
Sep 14 - Sep 17
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 a fitness center. Popular attractions United Center and Chicago Riverwalk are located nearby.
I love the pool and exercise room access, breakfast was amazing
Reviewed on Jul 1, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,582, price is now $1,077 per person
$1,077
per person
Aug 13 - Aug 17
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.
Excellente
Reviewed on Jul 1, 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
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Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Aug 11 - Fri, Aug 14
TPA
Tampa Intl.
RFD
Greater Rockford
$289 Roundtrip, found 1 day ago
$289
Roundtrip
found 1 day ago

Tue, Jul 14 - Tue, Jul 21
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$345 Roundtrip, found 4 days ago
$345
Roundtrip
found 4 days ago

Fri, Aug 28 - Sun, Aug 30
MCO
Orlando Intl.
RFD
Greater Rockford
$346 Roundtrip, found 1 day ago
$346
Roundtrip
found 1 day ago

Fri, Jul 17 - Sun, Jul 19
MSP
Minneapolis - St. Paul Intl.
RFD
Greater Rockford
$439 Roundtrip, found 6 days ago
$439
Roundtrip
found 6 days ago
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