Northwest Side Vacations from $557

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The Latest Northwest Side vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Hotel Riu Plaza Chicago
Level Chicago – Old Town
The Emily Hotel
Sable at Navy Pier Chicago, Curio Collection by Hilton
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Where to stay in Northwest Side

Find the best Northwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Northwest Side

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What to do in Northwest Side

Northwest Side Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $177 total per night from Jul 2 to Jul 3
$177 total
Jul 2 - Jul 3
Total with taxes and fees
8/10 Very Good! (10,184 reviews)
"This place was really horrible! The shower was cold as hell and the front desk didn't do anything to help. The room was not wiped down properly and I left first thing on the A.M. when I told the front desk about my stay, they did nothing to fix the issue or reimburse me a portion of my money. I came ..."

Reviewed on Jul 1, 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $215 total per night from Jul 5 to Jul 6
$215 total
Jul 5 - Jul 6
Total with taxes and fees
9.2/10 Wonderful! (1,823 reviews)
"Very clean, great location. Every staff member we encountered was just terrific"

Reviewed on Jun 30, 2026

Omni Chicago Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $189 total per night from Jul 9 to Jul 10
$189 total
Jul 9 - Jul 10
Total with taxes and fees
9/10 Wonderful! (4,474 reviews)
"Friendly staff. Our room was comfortable and clean."

Reviewed on Jun 30, 2026

Hilton Chicago/Magnificent Mile Suites
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.

Find the Best Northwest Side Vacation Packages

Northwest Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.