North Side Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top North Side vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Holiday Inn Chicago North-Evanston by IHG
Downtown Evanston
8.6/10 Excellent! (2,108 reviews)
Nov 24 - Nov 30
6 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $998, price is now $677 per person
$677
per person
found 1 day ago
4.5-star property
Swissotel - Chicago
Downtown Chicago
9/10 Wonderful! (3,512 reviews)
Oct 16 - Oct 19
3 night stay
Boston (BOS) to Chicago (ORD)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,508, price is now $908 per person
$908
per person
found 1 day ago
Lovely room
Reviewed on Sep 15, 2026
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9.2/10 Wonderful! (520 reviews)
Nov 11 - Nov 15
4 night stay
Boston (BOS) to Chicago (ORD)
Delta • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Coach
Save 100% on your flight
Price was $1,184, price is now $764 per person
$764
per person
found 1 day ago
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,681 reviews)
Oct 16 - Oct 19
3 night stay
Boston (BOS) to Chicago (ORD)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,361, price is now $906 per person
$906
per person
found 1 day ago
We were so excited about spending the time at Sable hotel however, when we arrived, it was the House of horrors. It was very filthy. Went to go grab an extra blanket and a butt plug fell out of it. Asked for them to please come clean the room they said housekeeping was not there and would take care of it tomorrow so we spent the first night in a filthy dirty room as they had no extra room rooms due to multiple concerts being held that weekend. My advice the location is great, but there’s other options that are more affordable.
Reviewed on Sep 14, 2026
Top rated hotels for your North Side vacation package
The Majestic Hotel
528 W Brompton Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.97 mi from city center
$199 nightly
The price is $234 total per night
$234 total
Sep 20 - Sep 21
Total with taxes and fees
Guests of The Majestic Hotel enjoy access to free WiFi in public areas, coffee in a common area, and a meeting room. Limited parking is available. Front-desk staff can answer questions 24/7, and assist with securing valuables, luggage storage, and concierge services. Other amenities at this boutique hotel include laundry facilities and a fireplace in the lobby.
Free WiFi
Air conditioning
The Willows Hotel
555 W Surf St Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.75 mi from city center
$174 nightly
The price is $204 total per night
$204 total
Sep 21 - Sep 22
Total with taxes and fees
Guests of The Willows Hotel enjoy free WiFi in public areas, coffee in a common area, and a fireplace in the lobby. Front-desk staff can answer questions 24/7, and assist with concierge services, securing valuables, and luggage storage. This boutique hotel also has a vending machine.
Free WiFi
Air conditioning
Hotel Lincoln
1816 N Clark Street Chicago IL
2.55 mi from city center
$178 nightly
The price is $209 total per night
$209 total
Sep 28 - Sep 29
Total with taxes and fees
Guests staying at Hotel Lincoln enjoy a 24-hour gym, a rooftop terrace, and free WiFi in public areas. Valet parking is available for USD 75 per day. The front desk has multilingual staff on hand 24/7 to help with dry cleaning/laundry, luggage storage, and tours or tickets. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this boutique hotel include a 24-hour business center, a microwave in a common area, and a computer station.
Pet friendly
Free WiFi
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.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Chicago CityPASS®: Experience 5 must-see attractions
$144
per adult
94% of travellers recommend
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