Oakton Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Oakton Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Aug 5 - Aug 12
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
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 staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
per person
Aug 5 - Aug 12
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
per person
Sep 1 - Sep 7
found 1 day ago
Roundtrip flight included
Houston (IAH) 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 5 - Aug 12
found 20 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
per person
Aug 5 - Aug 12
found 20 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Top Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
26.05 km from Oakton
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. ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
26.44 km from Oakton
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
26.05 km from Oakton
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 ...
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
26.63 km from Oakton
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
27.45 km from Oakton
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
The Wade
644 N Lake Shore Dr, Chicago, IL
26.87 km from Oakton
Stay at this 4.5-star luxury hotel in Chicago. Enjoy room service, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff ...
Hotel Felix River North/Magnificent Mile
111 W Huron St, Chicago, IL
25.68 km from Oakton
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 ...
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl, Chicago, IL
25.84 km from Oakton
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 ...
Swissotel - Chicago
323 E Wacker Dr, Chicago, IL
27 km from Oakton
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 ...
Freehand Chicago
19 East Ohio Street, Chicago, IL
26.13 km from Oakton
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. ...
River Hotel
75 East Wacker Drive, Chicago, IL
26.53 km from Oakton
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 ...
Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
27.44 km from Oakton
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
201 East Walton Place, Chicago, IL
26.08 km from Oakton
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Aug 5 - Sat, Aug 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$159 Roundtrip, found 5 days ago
$159
Roundtrip
found 5 days ago
Fri, Aug 29 - Tue, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$205 Roundtrip, found 6 days ago
$205
Roundtrip
found 6 days ago
Fri, Aug 22 - Sun, Aug 31
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$209 Roundtrip, found 18 hours ago
$209
Roundtrip
found 18 hours ago
Fri, Aug 22 - Sun, Aug 31
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$213 Roundtrip, found 18 hours ago
$213
Roundtrip
found 18 hours ago
Tue, Aug 5 - Sat, Aug 9
LAX
Los Angeles Intl.
MDW
Midway Intl.
$257 Roundtrip, found 5 days ago
$257
Roundtrip
found 5 days ago
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