Streeterville Vacation Packages for 2025

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

Choose two or more items and save on your trip:

Streeterville Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
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 8 - Jul 12
found 23 hours ago
Roundtrip flight included
Denver (DEN) 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.

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 8 - Jul 12
found 23 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Chicago River Side Suites

Chicago River Side Suites

2 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 8 - Jul 12
found 23 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, daily housekeeping, and slippers. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 8 - Jul 12
found 23 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 8 - Jul 12
found 23 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 8 - Jul 12
found 23 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Don't see what you're looking for?
See all available trips from Columbus to Streeterville
View all trips

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 ...
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 ...
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 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.
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
Don't see what you're looking for?
See all available properties in Streeterville
View all properties
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
Sat, Jul 5 - Wed, Jul 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 3 days ago
$110
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sat, Jul 5 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jul 9, priced at $110 found 3 days ago
Frontier Airlines
Sat, Jul 19 - Sun, Jul 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$188 Roundtrip, found 4 days ago
$188
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Jul 19 from Los Angeles Intl. to O'Hare Intl., returning Sun, Jul 20, priced at $188 found 4 days ago
Delta
Sat, Jul 5 - Wed, Jul 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$257 Roundtrip, found 3 days ago
$257
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Jul 5 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jul 9, priced at $257 found 3 days ago
American Airlines
Sat, Jul 5 - Wed, Jul 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$257 Roundtrip, found 3 days ago
$257
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jul 5 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jul 9, priced at $257 found 3 days ago