Streeterville Vacation Packages for 2025

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

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Streeterville 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
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
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 rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
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 the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.

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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 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 room service, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff ...
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 ...
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
Stay at this 4-star business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the ...
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
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 ...
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
163 East Walton Place, Chicago, IL
0.72 km from Streeterville
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street, Chicago, IL
0.27 km from Streeterville
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff ...
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 4-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street, Chicago, IL
0.12 km from Streeterville
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
301 E North Water St, Chicago, IL
0.52 km from Streeterville
Stay at this 4-star eco-certified hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
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
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
Loews Chicago Hotel

Loews Chicago Hotel

4.5 out of 5
455 North Park Drive, Chicago, IL
0.41 km from Streeterville
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
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 3-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the bar in our reviews. Popular ...
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
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful ...
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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
Tue, Jun 24 - Mon, Jul 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 4 days ago
$138
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Jun 24 from Los Angeles Intl. to O'Hare Intl., returning Mon, Jul 7, priced at $138 found 4 days ago
Spirit Airlines
Tue, Jun 24 - Mon, Jul 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$159 Roundtrip, found 4 days ago
$159
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Jun 24 from Los Angeles Intl. to O'Hare Intl., returning Mon, Jul 7, priced at $159 found 4 days ago
Frontier Airlines
Thu, Jul 24 - Sat, Jul 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$192 Roundtrip, found 5 days ago
$192
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Jul 24 from Los Angeles Intl. to O'Hare Intl., returning Sat, Jul 26, priced at $192 found 5 days ago
Hawaiian Airlines
Sat, Oct 11 - Wed, Oct 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 2 days ago
$216
Roundtrip
found 2 days ago
Select Hawaiian Airlines flight, departing Sat, Oct 11 from Los Angeles Intl. to O'Hare Intl., returning Wed, Oct 15, priced at $216 found 2 days ago