Deals on vacations and trips to Lakeside

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Lakeside flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Chicago/ Schaumburg

Hyatt Place Chicago/ Schaumburg

3 out of 5
Price was $351, price is now $221 per person
$221
per person
Jan 17 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a gym and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like cooked-to-order breakfast and free self parking.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $907, price is now $514 per person
$514
per person
Feb 10 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,048, price is now $647 per person
$647
per person
Feb 23 - Feb 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) 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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $972, price is now $602 per person
$602
per person
Feb 10 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $791, price is now $494 per person
$494
per person
Feb 23 - Feb 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Top Lakeside hotels deals

1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More

1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More

Lakeside MI
Get rates
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

Blue Chip Casino Hotel and Spa

3.5 out of 5
777 Blue Chip Drive Michigan City IN
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $121 total per night
$121 total
Jan 1 - Jan 2, 2026
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

Four Winds Casino Resort – New Buffalo

3.5 out of 5
11111 Wilson Road New Buffalo MI
Free Cancellation
$109 nightly
The price is $115 total per night
$115 total
Dec 21 - Dec 22
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

Baymont by Wyndham New Buffalo

2.5 out of 5
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
Jan 5 - Jan 6, 2026
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

Baymont by Wyndham Michigan City

2.5 out of 5
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
Jan 4 - Jan 5, 2026
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

Quality Inn Near Interstate I94

2.5 out of 5
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 24 - Dec 25
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
Don't see what you're looking for?
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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

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.

Eleanor O'Connor Wilson Woods Preserve

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.

Burnison Galleries

Frequently asked questions

How much are vacation packages to Lakeside?
Packages, including flights and hotels in Lakeside, start from as little as $221. Turn your daydreams into reality and secure your dream vacation with Travelocity today.
How long should my Lakeside vacation be?
Around 2 nights is the average amount of time visitors spend in Lakeside. But the perfect trip length depends on how many treasured memories you want to make. Why not stay a couple of extra days and explore some off-the-beaten-path gems?
Where can I get the best vacation package deals for Lakeside?
No matter how you like to travel, Travelocity can help you score an unbeatable Lakeside package deal. All you need to do is select a combination from our 400 partner airlines and 1,000,000 worldwide properties.
Why should I purchase my Lakeside vacation package via Travelocity?
From amazing destinations to fun experiences, we have everything you need to satisfy your travel desires. Our 24/7 customer support will also make sure you're being taken care of before, during and after your trip. And don't stress if you notice a better price on your booking, we'll match it. That's our Price Match Guarantee.
Can I save money on my Lakeside car rental if I bundle it with a hotel or flight?
Sure can — combine your hotel, flight and car into a Lakeside vacation package and you can save plenty. With so much to uncover in Lakeside, having your own set of wheels will make exploring a joy. Once you've buckled yourself in, put the stereo on and make your way to Wrigley Field, a renowned attraction roughly 50 mi from Lakeside.
Which airport is best for Lakeside?
Lakeside has a couple of major airports to jet into — Midway Intl. Airport (MDW) (55 mi away from the city center) and South Bend Intl. Airport (SBN) (20 mi away from central Lakeside).
What is there to do in Lakeside?
Burnison Galleries is one of the awesome sights that make Lakeside such a tourist hot spot. But leave some extra time to explore the city's lesser-known attractions too. This is often where the best vacation memories are made.
Where should I stay when visiting Lakeside?
If you're searching for somewhere to lay your head, take a look at the Lakeside Cottage Short Walk To Association Beach!. It's the top choice for many travelers.

Photos of local treasures

Browse Lakeside vacation photos for more inspiration