Exclusive Milwaukee Avenue Vacation Deals
Milwaukee Avenue vacation package deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $745, price is now $453 per person
$453
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Art Villa
West Town
Save 100% on your flight
Price was $1,110, price is now $664 per person
$664
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $723, price is now $457 per person
$457
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $770, price is now $506 per person
$506
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $745, price is now $493 per person
$493
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,686, price is now $1,122 per person
$1,122
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Top Milwaukee Avenue hotel deals
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
This apartment features limo/town car service, a garden, and barbecue grills.
Breakfast included
Kitchen
Holiday Inn Chicago North Shore by IHG
5300 West Touhy Ave, Skokie, IL
Free Cancellation
$107 nightly
The price is $123 total per night
$123 total
Nov 16 - Nov 17
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Enjoy the gym and perks like free self parking.
Pool
Hot Tub
Holiday Inn Chicago O'Hare Area by IHG
5615 North Cumberland Avenue, Chicago, IL
Free Cancellation
$87 nightly
The price is $102 total per night
$102 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Free self parking, a coffee shop, and a snack bar/deli are also offered.
Free airport shuttle
Pet friendly
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View all propertiesLowest 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.