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Near North Side Vacation Packages

Near North Side Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
Save 100% on your flight
Price was $403, price is now $292 per person
$292
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free parking, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and Topgolf are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,599, price is now $927 per person
$927
per person
Nov 12 - Nov 17
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) 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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,651, price is now $1,060 per person
$1,060
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $985, price is now $681 per person
$681
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $683, price is now $479 per person
$479
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,959, price is now $1,406 per person
$1,406
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
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 and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $973, price is now $706 per person
$706
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park 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
Price was $972, price is now $708 per person
$708
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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 Chicago Riverwalk are located nearby.

3-4 Night Vacations in Near North Side

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $394, price is now $263 per person
$263
per person
Dec 3 - Dec 6
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $697, price is now $453 per person
$453
per person
Dec 3 - Dec 6
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $833, price is now $552 per person
$552
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,244, price is now $828 per person
$828
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Near North Side

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $694, price is now $459 per person
$459
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,059, price is now $1,190 per person
$1,190
per person
Nov 12 - Nov 17
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,599, price is now $927 per person
$927
per person
Nov 12 - Nov 17
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,651, price is now $1,060 per person
$1,060
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

Cheap Hotel Deals in Near North Side

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
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 ...
Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowThe Chicago Hotel Collection - Magnificent Mile
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowThe Wade
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InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our ...
Opens in a new windowInterContinental Chicago Magnificent Mile by IHG
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
Opens in a new windowWarwick Allerton - Chicago
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
127 West Huron, at LaSalle Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, and a 24-hour fitness center. Our guests praise the helpful staff and ...
Opens in a new windowThe Godfrey Hotel Chicago
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
162 East Ontario Street Chicago IL
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 ...
Opens in a new windowHotel Saint Clair- Magnificent Mile
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
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 ...
Opens in a new windowEurostars Magnificent Mile
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

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Fri, Nov 13 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 2 hours ago
$197
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Fri, Nov 13 from Los Angeles Intl. to O'Hare Intl., returning Fri, Nov 13, priced at $197 found 2 hours ago
United
Fri, Nov 13 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 2 hours ago
$197
Roundtrip
found 2 hours ago
Select United flight, departing Fri, Nov 13 from Los Angeles Intl. to O'Hare Intl., returning Fri, Nov 13, priced at $197 found 2 hours ago
Frontier Airlines
Thu, Nov 19 - Sat, Dec 5
LAX
Los Angeles Intl.
MDW
Midway Intl.
$218 Roundtrip, found 5 days ago
$218
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Nov 19 from Los Angeles Intl. to Midway Intl., returning Sat, Dec 5, priced at $218 found 5 days ago
Philippine Airlines
Fri, Nov 13 - Wed, Dec 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$928 Roundtrip, found 6 hours ago
$928
Roundtrip
found 6 hours ago
Select Philippine Airlines flight, departing Fri, Nov 13 from Pudong Intl. to O'Hare Intl., returning Wed, Dec 2, priced at $928 found 6 hours ago