Search Deals onWinthrop Harbor Vacation Packages
Winthrop Harbor 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 $923, price is now $587 per person
$587
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 $1,991, price is now $1,169 per person
$1,169
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
Level Chicago Fulton Market
Save 100% on your flight
Price was $1,317, price is now $847 per person
$847
per person
Oct 18 - Oct 21
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.
Loved the hotel, super nice and clean! Felt like home away from home!
Reviewed on Sep 1, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,016, price is now $663 per person
$663
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Albuquerque (ABQ) 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.
We absolutely loved this hotel. My wife and I came for two days to celebrate my birthday. The location is fantastic to walk many great places, breakfast buffet was the best, excellent selection and tasty. While eating breakfast then brought me a birthday brownie and put chocolate in our room. Above and beyond expectations. Very clean and modern hotel with great staff. Roof top bar is a must!
Reviewed on Sep 2, 2026
Swissotel - Chicago
Save 100% on your flight
Price was $1,378, price is now $909 per person
$909
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.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,548, price is now $1,032 per person
$1,032
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Albuquerque (ABQ) 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
InterContinental Chicago Magnificent Mile by IHG
Save 100% on your flight
Price was $1,691, price is now $1,180 per person
$1,180
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
A fantastic day experience.
Reviewed on Sep 2, 2026
The Godfrey Hotel Chicago
Save 100% on your flight
Price was $1,044, price is now $730 per person
$730
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, 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.
Winthrop Harbor Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Winthrop Harbor 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.
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Fri, Nov 6 - Mon, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Fri, Nov 6 - Mon, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Sat, Sep 5 - Wed, Sep 16
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,185 Roundtrip, found 2 hours ago
$1,185
Roundtrip
found 2 hours ago
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