Deals on vacations and trips to Lakeside
Save when you book Lakeside package deals
Lakeside flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $308, price is now $150 per person
$150
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Limo/town car service, WiFi in public areas, and express check-out are also on offer.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $384, price is now $196 per person
$196
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Holiday Inn Chicago - Schaumburg by IHG
Save 100% on your flight
Price was $447, price is now $237 per person
$237
per person
Dec 26 - Dec 31
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free parking, a snack bar/deli, and a computer station are also offered.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $493, price is now $263 per person
$263
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $1,009, price is now $547 per person
$547
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Top Lakeside hotels deals
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Lakeside MI
This cottage features an outdoor pool and a hot tub. Families will appreciate the playground and barbecue grills. A garden and laundry facilities are also provided.
Pool
Hot Tub
Blue Chip Casino Hotel and Spa
777 Blue Chip Drive Michigan City IN
Free Cancellation
Reserve now, pay when you stay
$96 nightly
The price is $108 total per night
$108 total
Dec 2 - Dec 3
Total with taxes and fees
This hotel features a casino, a full-service spa, and 3 restaurants. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. There's a bar/lounge on site, and a coffee shop and wedding services are also provided.
Spa
Free WiFi
Four Winds Casino Resort – New Buffalo
11111 Wilson Road, New Buffalo, MI
Free Cancellation
$84 nightly
The price is $89 total per night
$89 total
Nov 24 - Nov 25
Total with taxes and fees
A casino, 4 restaurants, and 2 hot tubs are all featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and free valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy free perks like free self parking and an area shuttle.
Pool
Hot Tub
Baymont by Wyndham New Buffalo
18800 Harbor Country Drive, New Buffalo, MI
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $71 total per night
$71 total
Nov 25 - Nov 26
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Baymont by Wyndham Michigan City
4128 South Franklin Street Michigan City IN
Free Cancellation
Reserve now, pay when you stay
$69 nightly
The price is $77 total per night
$77 total
Nov 19 - Nov 20
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like full breakfast and free self parking.
Pool
Hot Tub
Quality Inn Near Interstate I94
18830 Laporte Rd New Buffalo MI
Free Cancellation
Reserve now, pay when you stay
$68 nightly
The price is $72 total per night
$72 total
Dec 1 - Dec 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Enjoy the hot tub and free perks like on-the-go breakfast and free self parking. A business center, free WiFi in public areas, and a picnic area are also on offer.
Pool
Hot Tub
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.
Popular places to visit
Burnison Galleries
You can spend time studying the exhibits at Burnison Galleries in Lakeside. Stroll along the beautiful beaches or visit the casinos in this romantic area.
Eleanor O'Connor Wilson Woods Preserve
You can take time to visit Eleanor O'Connor Wilson Woods Preserve during your travels to Lakeside. Stroll along the lakeside or discover the area's sunsets.
Frequently asked questions
Photos of local treasures
Browse Lakeside vacation photos for more inspiration
