Search Deals onWinfield Vacation Packages
Winfield 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 $804, price is now $471 per person
$471
per person
Nov 11 - Nov 14
found 13 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Location and facility was very nice
Reviewed on Sep 7, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,214, price is now $741 per person
$741
per person
Oct 22 - 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 breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The roof top is not available all day, and the gym was small, no pool, For the price you pay for these things listed a resort fees is ridiculous
I also had to ask for a shower cap and there is no ice machines or bucket. One bottle of water was in the room for two. RUI could do better.
The breakfast is fabulous I must say.
Reviewed on Sep 8, 2026
Level Chicago Fulton Market
Save 100% on your flight
Price was $1,465, price is now $940 per person
$940
per person
Oct 15 - Oct 19
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 pool & jacuzzi was perfect, this hotel is beautiful
Reviewed on Sep 7, 2026
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,364, price is now $895 per person
$895
per person
Nov 12 - Nov 15
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.
Fantastic views, hotel was first class!
Reviewed on Sep 8, 2026
Chicago Marriott Downtown Magnificent Mile
Save 100% on your flight
Price was $810, price is now $538 per person
$538
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Good location
Reviewed on Sep 6, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,477, price is now $1,004 per person
$1,004
per person
Oct 15 - Oct 19
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.
The Talbott, Autograph Collection
Price was $861, price is now $602 per person
$602
per person
Nov 12 - Nov 15
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 helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Loved our stay!!!
Reviewed on Sep 8, 2026
The Wade
Price was $750, price is now $526 per person
$526
per person
Nov 12 - Nov 15
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 room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
When we arrived the room was not ready however we have arrived around 6 pm. We went to this hotel for our anniversary but the receptionist offered us to stay in a room with 2 single bed. However thankfully soon after our room got ready. But overall the hotel was not clean at all.
Reviewed on Sep 8, 2026
Winfield Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Winfield 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.
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$164 Roundtrip, found 1 hour ago
$164
Roundtrip
found 1 hour ago
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Mon, Sep 28 - Tue, Oct 6
LAX
Los Angeles Intl.
MDW
Midway Intl.
$261 Roundtrip, found 21 hours ago
$261
Roundtrip
found 21 hours ago
Fri, Nov 13 - Mon, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,068 Roundtrip, found 3 hours ago
$1,068
Roundtrip
found 3 hours ago
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