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Oak Street Vacation Packages

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Oak Street Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Chicago-Downers Grove by IHG

Holiday Inn Express Chicago-Downers Grove by IHG

2.5 out of 5
per person
May 24 - May 28
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Downers Grove. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Yorktown Shopping Center and Morton Arboretum are located nearby.
Admiral Motel By Oyo Chicago I-94

Admiral Motel By Oyo Chicago I-94

2.5 out of 5
per person
May 30 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free parking, room service, and a 24-hour front desk. Popular attractions Chicago Museum of Science and Industry and Calumet Park are located nearby.
DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
per person
May 30 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Naperville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Arrowhead Golf Club are located nearby.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
per person
Jun 4 - Jun 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Holiday Inn Express & Suites Chicago - Oak Forest by IHG

Holiday Inn Express & Suites Chicago - Oak Forest by IHG

2.5 out of 5
per person
Jun 9 - Jun 13
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Oak Forest. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Popular attractions George Dunne National Golf Club and Oak Hill Park are located nearby.
Crowne Plaza Lombard Downers Grove by IHG

Crowne Plaza Lombard Downers Grove by IHG

3.5 out of 5
per person
Jun 9 - Jun 13
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Glen Ellyn. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Lilacia Park and Yorktown Shopping Center are located nearby.
Holiday Inn Express & Suites Prospect Heights by IHG

Holiday Inn Express & Suites Prospect Heights by IHG

3 out of 5
per person
May 30 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Prospect Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions River Trail Nature Center and Northbrook Sports Complex are located nearby.
DoubleTree by Hilton Chicago - Arlington Heights

DoubleTree by Hilton Chicago - Arlington Heights

4 out of 5
per person
Jun 9 - Jun 13
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Arlington Heights. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and Allstate Arena are located nearby.
Super 8 by Wyndham Bridgeview/Chicago Area

Super 8 by Wyndham Bridgeview/Chicago Area

2 out of 5
per person
May 30 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Bridgeview. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SeatGeek Stadium and Chicago Ridge Shopping Mall are located nearby.
Hilton Garden Inn Naperville/Warrenville

Hilton Garden Inn Naperville/Warrenville

3 out of 5
per person
May 23 - May 28
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Warrenville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Nike Sports Complex and Topgolf are located nearby.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Holiday Inn Chicago SW-Countryside ConfCtr by IHG

Holiday Inn Chicago SW-Countryside ConfCtr by IHG

3.5 out of 5
per person
Jun 9 - Jun 13
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Countryside. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Flagg Creek Golf Course and Park District of La Grange are located nearby.

3-4 Night Vacations in Oak Street

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

2 out of 5
per person
Jun 14 - Jun 17
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90

2 out of 5
Woodlawn
per person
Jun 14 - Jun 17
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
per person
Jun 14 - Jun 17
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Oak Street

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago SW-Countryside ConfCtr by IHG

Holiday Inn Chicago SW-Countryside ConfCtr by IHG

3.5 out of 5
per person
May 23 - May 28
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Admiral Motel By Oyo Chicago I-94

Admiral Motel By Oyo Chicago I-94

2.5 out of 5
Chatham
per person
May 30 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Four Points by Sheraton Chicago O'Hare Airport

Four Points by Sheraton Chicago O'Hare Airport

3 out of 5
O'Hare
per person
May 30 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
per person
May 30 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)

Oak Street Last Minute Hotel Deals

Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
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 ...
Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
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. ...
Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and ...
Swissotel - Chicago
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
The Westin Michigan Avenue Chicago
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
Hotel Felix River North/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3 out of 5
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. ...
Hilton Garden Inn Chicago Downtown/Magnificent Mile
The Royal Sonesta Chicago River North
The Royal Sonesta Chicago River North
4.5 out of 5
505 N State Street, Chicago, IL
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 ...
The Royal Sonesta Chicago River North
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
See all 3,702 properties in Oak Street
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.