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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.
Embassy Suites by Hilton Chicago Naperville

Embassy Suites by Hilton Chicago Naperville

3.5 out of 5
Save 100% on your flight
per person
Jun 18 - Jun 22
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Naperville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Nike Sports Complex are located nearby.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and a 24-hour fitness center. 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.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool 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
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (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.
Hampton Inn Chicago-Carol Stream

Hampton Inn Chicago-Carol Stream

2.5 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 23
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Embassy Suites by Hilton Chicago Naperville

Embassy Suites by Hilton Chicago Naperville

3.5 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 23
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

5-7 Night Vacations in Near North Side

Price found within the past 48 hours. Click for updated prices.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
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 1 - Jul 6
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

Cheap Hotel Deals in Near North Side

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
909 North Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
The Westin Michigan Avenue Chicago
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Stay at this 4-star family-friendly hotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and in-room massages. Our guests praise the ...
Warwick Allerton - Chicago
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
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
Embassy Suites by Hilton Chicago Downtown River North
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Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Holiday Inn Chicago Dwtn - The Mart by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
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 ...
Hilton Chicago/Magnificent Mile Suites
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St, Chicago, IL
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 ...
Hotel Felix River North/Magnificent Mile
Ambassador Hotel Chicago

Ambassador Hotel Chicago

4 out of 5
1301 N State Pkwy, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Ambassador Hotel Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Hilton Garden Inn Chicago Downtown/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.

Frontier Airlines
Wed, May 28 - Sat, May 31
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$91 Roundtrip, found 1 day ago
$91
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, May 28 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 31, priced at $91 found 1 day ago
Spirit Airlines
Wed, Jun 18 - Tue, Jun 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Jun 18 from Los Angeles Intl. to O'Hare Intl., returning Tue, Jun 24, priced at $100 found 1 day ago
Frontier Airlines
Wed, May 28 - Tue, Jun 3
LAX
Los Angeles Intl.
MDW
Midway Intl.
$214 Roundtrip, found 11 hours ago
$214
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Wed, May 28 from Los Angeles Intl. to Midway Intl., returning Tue, Jun 3, priced at $214 found 11 hours ago
Icelandair
Tue, Aug 26 - Tue, Sep 2
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$543 Roundtrip, found 2 days ago
$543
Roundtrip
found 2 days ago
Select Icelandair flight, departing Tue, Aug 26 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Tue, Sep 2, priced at $543 found 2 days ago