Cheap flights To Sycamore (CHI) from $85
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Cheap Flights to Sycamore from $85 One Way, $173 Round Trip
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
IAH
George Bush Intercontinental
RFD
Greater Rockford
$173 Roundtrip, found 2 days ago
$173
Roundtrip
found 2 days ago
BOS
Logan Intl.
RFD
Greater Rockford
$176 Roundtrip, found 6 days ago
$176
Roundtrip
found 6 days ago
IAH
George Bush Intercontinental
RFD
Greater Rockford
$188 Roundtrip, found 6 days ago
$188
Roundtrip
found 6 days ago
BOS
Logan Intl.
RFD
Greater Rockford
$195 Roundtrip, found 5 days ago
$195
Roundtrip
found 5 days ago
BOS
Logan Intl.
RFD
Greater Rockford
$196 Roundtrip, found 11 hours ago
$196
Roundtrip
found 11 hours ago
LAX
Los Angeles Intl.
RFD
Greater Rockford
$199 Roundtrip, found 3 days ago
$199
Roundtrip
found 3 days ago
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$201 Roundtrip, found 2 days ago
$201
Roundtrip
found 2 days ago
BOS
Logan Intl.
RFD
Greater Rockford
$205 Roundtrip, found 11 hours ago
$205
Roundtrip
found 11 hours ago
DEN
Denver Intl.
RFD
Greater Rockford
$205 Roundtrip, found 6 days ago
$205
Roundtrip
found 6 days ago
IAH
George Bush Intercontinental
RFD
Greater Rockford
$208 Roundtrip, found 3 days ago
$208
Roundtrip
found 3 days ago
Sycamore Flight Information
Traveling To | Sycamore |
|---|---|
Destination Airport IATA Code | CHI |
Number of Airlines Serving | |
Airlines | American Airlines |
Flight Price | $173 |
Earliest Departing Flight | |
Latest Departing Flight |
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Sycamore economy flight packages
Price found within the past 48 hours. Click for updated prices.
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View all tripsSycamore premium economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Swissotel - Chicago
9/10 Wonderful! (3,303 reviews)
Jun 30 - Jul 5
5 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • PremiumEconomy
Price was $1,399, price is now $1,016 per person
$1,016
per person
found 1 day ago
Great stay and we highly recommend. We will be back.
Reviewed on Apr 21, 2026
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (4,070 reviews)
Jun 30 - Jul 5
5 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • PremiumEconomy
Price was $1,563, price is now $1,124 per person
$1,124
per person
found 1 day ago
Great location, clean, and great breakfast buffet
Reviewed on Mar 8, 2026
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
9.4/10 Exceptional! (2,478 reviews)
Jun 30 - Jul 5
5 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,986, price is now $1,492 per person
$1,492
per person
found 1 day ago
Really nice property, rooms were clean, and staff was extremely friendly
Reviewed on May 5, 2026
Sycamore business class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
DoubleTree by Hilton Libertyville - Mundelein
8.6/10 Excellent! (1,000 reviews)
Jun 10 - Jun 13
3 night stay
San Juan (SJU) to Chicago (ORD)
American Airlines • BusinessClass
Chicago (ORD) to San Juan (SJU)
Frontier Airlines • BusinessClass
Price was $1,070, price is now $1,016 per person
$1,016
per person
found 1 day ago
Very nice. Clean nest rooms, nicely appointed facility
Reviewed on Mar 5, 2026
2.0-star property
Illinois Beach Hotel
8/10 Very Good! (516 reviews)
Jun 10 - Jun 13
3 night stay
San Juan (SJU) to Chicago (ORD)
American Airlines • BusinessClass
Chicago (ORD) to San Juan (SJU)
Frontier Airlines • BusinessClass
Price was $1,124, price is now $1,022 per person
$1,022
per person
found 1 day ago
Private beach on Lake Michigan. Very beautiful.Nature trails right out side the door. Great staff . Good restaurant.
Reviewed on Oct 20, 2024
4.0-star property
Renaissance Chicago North Shore Hotel
8.4/10 Very Good! (1,001 reviews)
Jun 10 - Jun 13
3 night stay
San Juan (SJU) to Chicago (ORD)
American Airlines • BusinessClass
Chicago (ORD) to San Juan (SJU)
Frontier Airlines • BusinessClass
Price was $1,135, price is now $1,076 per person
$1,076
per person
found 1 day ago
Professional friendly staff
Reviewed on Jan 19, 2026
Sycamore first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
DoubleTree by Hilton Chicago Schaumburg
7.2/10 Good! (1,006 reviews)
Jun 24 - Jun 27
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • FirstClass
Price was $673, price is now $590 per person
$590
per person
found 1 day ago
The wallpaper in the room was peeling off the wall. The pool was closed for the 3 days I was there.
Reviewed on Apr 20, 2026
5.0-star property
Trump International Hotel & Tower Chicago
9.4/10 Exceptional! (1,863 reviews)
Jun 30 - Jul 5
5 night stay
Dallas (DFW) to Chicago (ORD)
American Airlines • FirstClass
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • FirstClass
Price was $2,559, price is now $2,031 per person
$2,031
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!
Reviewed on Oct 13, 2025
5.0-star property
The Langham, Chicago
9.8/10 Exceptional! (1,006 reviews)
Jun 30 - Jul 5
5 night stay
Dallas (DFW) to Chicago (ORD)
American Airlines • FirstClass
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • FirstClass
Price was $2,181, price is now $1,881 per person
$1,881
per person
found 1 day ago
Just an absolutely beautiful hotel with spectacular service. Highly recommend.
Reviewed on Mar 29, 2024
Don't see what you're looking for?
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.