Lakeside Vacation Packages 2026 from $641

Lakeside flight + hotel vacation packages

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

Fairmont Chicago at Millennium Park

Downtown Chicago

Save 100% on your flight

$641

per person

Jun 23 - Jun 26

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$830

per person

Jul 8 - Jul 12

found 7 hours ago

Roundtrip flight included

Orlando (MCO) 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.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$678

per person

Jul 11 - Jul 14

found 1 day ago

Roundtrip flight included

Dallas (DAL) 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.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$1,030

per person

Jul 11 - Jul 14

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Chicago (ORD)

This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

ENVITAE Hotel

Near North Side

Save 100% on your flight

$1,726

per person

Jul 8 - Jul 13

found 7 hours ago

Roundtrip flight included

Orlando (MCO) to Chicago (ORD)

This hotel includes free WiFi in public areas and a virtual front desk.

Top Lakeside hotels deals

Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location

Lakeside MI

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

Kitchen

Washer

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

Lakeside MI

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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

$116 nightly

$130 total

May 3 - May 4

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. You'll appreciate the indoor pool, bar/lounge, and coffee shop.

Pool

Spa

Four Winds Casino Resort – New Buffalo

11111 Wilson Road New Buffalo MI

Free Cancellation

$109 nightly

$115 total

May 3 - May 4

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

Quality Inn Near Interstate I94

18830 Laporte Rd New Buffalo MI

Free Cancellation

$81 nightly

$86 total

May 4 - May 5

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

Holiday Inn Express & Suites New Buffalo by IHG

11500 Holiday Dr New Buffalo MI

Free Cancellation

$118 nightly

$125 total

May 5 - May 6

Total with taxes and fees

This hotel features an indoor pool and a gym. Enjoy the hot tub and free perks like buffet breakfast and free self parking. Free WiFi in public areas and a safe deposit box are also provided.

Pool

Hot Tub

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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.

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.

Frequently asked questions

How much are vacation packages to Lakeside?

Packages, including flights and hotels in Lakeside, start from as little as $641. 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.