Vacations Close To Oak Street

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

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Oak Street Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $372, price is now $253 per person
$253
per person
Jan 23 - Jan 27
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $599, price is now $397 per person
$397
per person
Jan 23 - Jan 27
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $453, price is now $313 per person
$313
per person
Jan 23 - Jan 27
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $515, price is now $359 per person
$359
per person
Jan 23 - Jan 27
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $465, price is now $325 per person
$325
per person
Jan 23 - Jan 27
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $585, price is now $416 per person
$416
per person
Jan 23 - Jan 27
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was $449, price is now $335 per person
$335
per person
Jan 23 - Jan 27
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was $356, price is now $266 per person
$266
per person
Jan 23 - Jan 27
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

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Best Lodging Options Near Oak Street

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
0.9 km from Oak Street
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
0.36 km from Oak Street
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

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl Chicago IL
0.19 km from Oak Street
Book a stay at this boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
0.74 km from Oak Street
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
1.44 km from Oak Street
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
120 East Delaware Place Chicago IL
0.21 km from Oak Street
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. ...
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue Chicago IL
0.67 km from Oak Street
Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
0.83 km from Oak Street
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 ...
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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.