Downtown Skokie Vacation Packages for 2026

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Downtown Skokie 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
Price was $1,408, price is now $895 per person
$895
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this 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.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,771, price is now $979 per person
$979
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
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 Riverwalk are located nearby.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,965, price is now $1,266 per person
$1,266
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,512, price is now $987 per person
$987
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,641, price is now $1,071 per person
$1,071
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,420, price is now $963 per person
$963
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

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Top Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
20.11 km from Downtown Skokie
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
17.97 km from Downtown Skokie
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 ...
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
18.31 km from Downtown Skokie
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
18.47 km from Downtown Skokie
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 ...
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
13.7 km from Downtown Skokie
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
18.82 km from Downtown Skokie
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 ...
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
18.61 km from Downtown Skokie
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. ...
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr Chicago IL
19.21 km from Downtown Skokie
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the ...
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
19.05 km from Downtown Skokie
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
19.25 km from Downtown Skokie
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
20.35 km from Downtown Skokie
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
18.16 km from Downtown Skokie
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
71 E Wacker Dr Chicago IL
18.9 km from Downtown Skokie
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
17.11 km from Downtown Skokie
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
18.88 km from Downtown Skokie
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
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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.

Frontier Airlines
Wed, Apr 15 - Wed, Apr 22
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 3 hours ago
$110
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Apr 15 from Los Angeles Intl. to O'Hare Intl., returning Wed, Apr 22, priced at $110 found 3 hours ago
Spirit Airlines
Sun, May 3 - Fri, May 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, May 3 from Los Angeles Intl. to O'Hare Intl., returning Fri, May 8, priced at $180 found 1 day ago
American Airlines
Wed, Apr 22 - Sat, May 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$241 Roundtrip, found 2 hours ago
$241
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Apr 22 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 9, priced at $241 found 2 hours ago
United
Wed, Apr 22 - Sat, May 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$241 Roundtrip, found 2 hours ago
$241
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Apr 22 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 9, priced at $241 found 2 hours ago
Delta
Wed, Apr 22 - Sat, May 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$261 Roundtrip, found 2 hours ago
$261
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Apr 22 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 9, priced at $261 found 2 hours ago