Deals on vacations and trips to Streeterville
Streeterville flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $457, price is now $284 per person
$284
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.
Art Villa
West Town
Save 100% on your flight
Price was $999, price is now $514 per person
$514
per person
Dec 31 - Jan 3
found 22 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $727, price is now $428 per person
$428
per person
Dec 30 - Jan 2
found 8 hours ago
Roundtrip flight included
Baltimore (BWI) 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.
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,779, price is now $1,084 per person
$1,084
per person
Dec 23 - Dec 27
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the indoor pool and perks like a free area shuttle.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $640, price is now $398 per person
$398
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, laundry facilities, and concierge services are also on offer.
Top Streeterville hotels deals
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $137 total per night
$137 total
Nov 16 - Nov 17
Total with taxes and fees
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.
Pet friendly
Free WiFi
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$97 nightly
The price is $114 total per night
$114 total
Nov 16 - Nov 17
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Breakfast included
Pet friendly
Sable at Navy Pier Chicago, Curio Collection by Hilton
900 E Grand, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$188 nightly
The price is $221 total per night
$221 total
Nov 9 - Nov 10
Total with taxes and fees
This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Free WiFi
Restaurant
Aloft Chicago Mag Mile
243 E. Ontario, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$123 nightly
The price is $144 total per night
$144 total
Nov 9 - Nov 10
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Valet parking, a business center, and a snack bar/deli are also offered.
Pool
Pet friendly
Hotel Riu Plaza Chicago
150 East Ontario Street, Chicago, IL
$153 nightly
The price is $180 total per night
$180 total
Nov 9 - Nov 10
Total with taxes and fees
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.
Breakfast included
Free WiFi
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
201 East Walton Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$128 nightly
The price is $150 total per night
$150 total
Nov 16 - Nov 17
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast and free WiFi. Traveling on business? Take advantage of the business center, express check-out, and valet parking. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
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.
Popular places to visit
Water Tower Place
4.5/5(834 reviews)
Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.
875 North Michigan Avenue
4.5/5(1,913 reviews)
You can find out about the history of Chicago with a visit to 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its fascinating museums.
Chicago Children's Museum
4.5/5(196 reviews)
You can take time to visit Chicago Children's Museum during your travels to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
Frequently asked questions
Photos of local treasures
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