Streeterville Vacation Packages for 2025

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Top Hotel Deals

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
0.71 km from Streeterville
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
0.7 km from Streeterville
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 ...
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
0.12 km from Streeterville
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 ...
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
900 E Grand Chicago IL
1.53 km from Streeterville
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful ...
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
165 East Ontario Street Chicago IL
0.06 km from Streeterville
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St Chicago IL
0.17 km from Streeterville
Book a stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the ...
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
0.09 km from Streeterville
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
162 East Ontario Street Chicago IL
0.08 km from Streeterville
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
0.55 km from Streeterville
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place Chicago IL
0.74 km from Streeterville
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 ...
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
633 N Saint Clair St Chicago IL
0.06 km from Streeterville
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4 out of 5
511 North Columbus Drive Chicago IL
0.27 km from Streeterville
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
108 East Superior Street Chicago IL
0.36 km from Streeterville
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition ...
Loews Chicago Hotel

Loews Chicago Hotel

4.5 out of 5
455 North Park Drive Chicago IL
0.41 km from Streeterville
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
The Drake

The Drake

4 out of 5
140 E Walton Place Chicago IL
0.79 km from Streeterville
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff ...
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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.

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.

Spirit Airlines
Wed, Dec 17 - Thu, Jan 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$183 Roundtrip, found 5 days ago
$183
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Dec 17 from Los Angeles Intl. to O'Hare Intl., returning Thu, Jan 1, priced at $183 found 5 days ago
Frontier Airlines
Thu, Dec 18 - Wed, Dec 31
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$225 Roundtrip, found 5 days ago
$225
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Dec 18 from Los Angeles Intl. to O'Hare Intl., returning Wed, Dec 31, priced at $225 found 5 days ago
Delta
Wed, Dec 17 - Tue, Dec 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$347 Roundtrip, found 3 days ago
$347
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Dec 17 from Los Angeles Intl. to O'Hare Intl., returning Tue, Dec 23, priced at $347 found 3 days ago
United
Sat, Jan 3 - Wed, Jan 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$452 Roundtrip, found 2 days ago
$452
Roundtrip
found 2 days ago
Select United flight, departing Sat, Jan 3 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jan 7, priced at $452 found 2 days ago
American Airlines
Sat, Jan 3 - Wed, Jan 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$471 Roundtrip, found 2 days ago
$471
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jan 3 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jan 7, priced at $471 found 2 days ago