Lakeside Vacation Packages 2026 from $369

Lakeside flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

$369

per person

Nov 23 - Nov 27

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. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A hair salon, express check-in, and express check-out are also on offer.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$981

per person

Nov 23 - Nov 27

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.

Chicago Lake Shore Hotel

Kenwood

Save 100% on your flight

$389

per person

Nov 26 - Dec 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Free self parking is available and the hotel's multilingual staff can provide around-the-clock assistance. WiFi in public areas is free. Luggage storage is also provided.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$527

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.

Eaglewood Resort and Spa

Save 100% on your flight

$487

per person

Nov 21 - Nov 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This smoke-free resort features a golf course, a full-service spa, and 2 restaurants. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.

Top Lakeside hotels deals

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

Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location

Lakeside MI

Get rates

This cottage features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Four Winds Casino Resort – New Buffalo

11111 Wilson Road New Buffalo MI

Free Cancellation

$109 nightly

$115 total

Sep 22 - Sep 23

Total with taxes and fees

A casino, 4 restaurants, and a 24-hour gym 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

Parking included

Blue Chip Casino Hotel and Spa

777 Blue Chip Drive Michigan City IN

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$140 total

Sep 27 - Sep 28

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

Quality Inn Near Interstate I94

18830 Laporte Rd New Buffalo MI

Free Cancellation

$81 nightly

$86 total

Oct 11 - Oct 12

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

Pine Lake Resort and Banquets

444 Pine Lake Ave La Porte IN

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$97 total

Sep 22 - Sep 23

Total with taxes and fees

A full-service spa, an indoor pool, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like continental breakfast and free self parking.

Pool

Breakfast included

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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.

Stay near popular Lakeside attractions

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.

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Frequently asked questions

How much are vacation packages to Lakeside?

Packages, including flights and hotels in Lakeside, start from as little as $369. 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.