
North Side Vacation Packages
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3.0-star property
Dorothy's
Lakeview
8.4/10 Very Good! (93 reviews)
May 2 - May 5
3 night stay
Boston (BOS) to Chicago (ORD)
Delta • Roundtrip • Coach
Price was $398, price is now $297 per person
$297
per person
found 23 hours ago
The room was small, but very comfortable. Initially, I was a bit leery of the "no reception; we'll send you a code" check-in, but it went very smoothly. The code worked on all the doors it was supposed to work on, and I appreciated the triple-layer of code security - outside door, door to the floor, door to the room. Dorothy's is ideally situated, and easy walking distance to attractions in the area, in addition to the Red line train and numerous bus lines. If I had to ding Dorothy's on anything, it's this: Coffeemate isn't cream and doesn't do the same in your coffee in the morning as does half-and-half.
Reviewed on Dec 31, 2025
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
$82 nightly
The price is $96 total per night
$96 total
Mar 8 - Mar 9
Total with taxes and fees
Renovated in 2025, The Majestic Hotel offers a gym, free WiFi in public areas, and coffee in a common area. 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 a meeting room, laundry facilities, and a fireplace in the lobby.
Free WiFi
Air conditioning

Hotel Lincoln
1816 N Clark Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
2.55 mi from city center
$102 nightly
The price is $120 total per night
$120 total
Feb 19 - Feb 20
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, tours or tickets, and luggage storage. 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

Hotel Versey Chicago Lincoln Park
644 West Diversey Parkway Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.65 mi from city center
$77 nightly
The price is $90 total per night
$90 total
Feb 23 - Feb 24
Total with taxes and fees
Hotel Versey Chicago Lincoln Park features free WiFi in public areas and a TV in a common area. Self parking is offered for USD 30.00 per day. The 24-hour front desk has multilingual staff ready to assist with tours/tickets and luggage storage.
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.
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