Search Deals onOak Street Vacation Packages
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Oak Street Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago - Alsip
Save 100% on your flight
Price was $499, price is now $293 per person
$293
per person
Dec 18 - Dec 23
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (MDW)
Stay at this 4-star business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hollywood Park and Gaelic Park are located nearby.
Trump International Hotel & Tower Chicago
Price was $1,577, price is now $996 per person
$996
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star 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.
Level Chicago – Old Town
Price was $937, price is now $461 per person
$461
per person
Dec 2 - Dec 8
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Level Chicago - River North
Price was $1,019, price is now $539 per person
$539
per person
Dec 2 - Dec 8
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Radisson Blu Aqua Hotel Chicago
Save 100% on your flight
Price was $931, price is now $507 per person
$507
per person
Dec 2 - Dec 8
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Royal Sonesta Chicago River North
Save 100% on your flight
Price was $726, price is now $425 per person
$425
per person
Dec 2 - Dec 8
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $659, price is now $407 per person
$407
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Chicago O'Hare Airport
Save 100% on your flight
Price was $1,238, price is now $799 per person
$799
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.
Swissotel - Chicago
Save 100% on your flight
Price was $484, price is now $313 per person
$313
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star 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.
Silversmith Hotel Chicago Downtown
Save 100% on your flight
Price was $699, price is now $460 per person
$460
per person
Dec 2 - Dec 8
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Sheraton Grand Chicago Riverwalk
Save 100% on your flight
Price was $627, price is now $413 per person
$413
per person
Dec 11 - Dec 16
found 14 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 4-star eco-certified hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Arista
Save 100% on your flight
Price was $709, price is now $471 per person
$471
per person
Dec 18 - Dec 23
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Naperville. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Topgolf and Odyssey Fun World are located nearby.
3-4 Night Vacations in Oak Street
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Oak Street
Price found within the past 48 hours. Click for updated prices.
Oak Street Last Minute Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl, Chicago, IL
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
Freehand Chicago
19 East Ohio Street, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Stay at this 4-star family-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Hotel Riu Plaza Chicago
150 East Ontario Street, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
Aloft Chicago Mag Mile
243 E. Ontario, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the bar in our reviews. Popular ...
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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