Lower West Side Holidays

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    Packages with flights are ATOL protected

Your Lower West Side Holiday

History, culture, food, fun — you'll find it all in Lower West Side. Discover the best of this neighbourhood with a holiday package to Lower West Side. Begin your trip to Lower West Side by heading to nearby attractions such as Willis Tower, University of Illinois Chicago and Skydeck Ledge. Whatever your dream Lower West Side holiday looks like, you can make it a reality with Expedia.

Price found within the past 48 hours. Click for updated prices.
  • Indoor wedding
    Aug 3 - Aug 8

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,349 reviews)
    "It was a nice room. Only complaint would be air conditioning. I don’t do hot. Hate sweating. Had turned to 65 and still not really cold. Otherwise overall nice."
    Reviewed May 26, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £1,867
    £1,354
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Smart TV
    Aug 2 - Aug 7

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (489 reviews)
    "Amazing place"
    Reviewed May 26, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 2 stops ORD - LHR • 2 stops
    £1,950
    £1,374
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Terrace/patio
    Jul 4 - Jul 11

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    7 nights
    5.0 star property
    9.6/10 - Exceptional (1,876 reviews)
    "The view from our room was awesome!!"
    Reviewed May 27, 2026
    Return • Edinburgh (EDI) - Chicago (ORD)
    EDI - ORD • Direct ORD - EDI • Direct
    £3,153
    £2,358
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • Seasonal outdoor pool, pool loungers
    Aug 2 - Aug 7

    Viceroy Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,230 reviews)
    "I don’t think I have ever encountered a more polite, charming, and informed staff. As someone who has worked in the service industry I assume that your training program does an excellent job. The hotel is beautiful and well maintained. We’ll be back."
    Reviewed May 25, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 2 stops ORD - LHR • 2 stops
    £1,921
    £1,465
    per traveller
    found 1 day ago
    Viceroy Chicago
  • Terrace/patio
    Jul 4 - Jul 11

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    7 nights
    4.0 star property
    9.4/10 - Exceptional (2,516 reviews)
    "Clean and have a beautiful view of the lake"
    Reviewed May 26, 2026
    Return • Edinburgh (EDI) - Chicago (ORD)
    EDI - ORD • Direct ORD - EDI • Direct
    £2,350
    £1,801
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton

Where to stay in Lower West Side

Find the best Lower West Side areas and neighborhoods for the activities you enjoy most. Learn more about Lower West Side
Downtown Chicago

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Top hotels in Lower West Side

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is £186 per night from 2 Jun to 3 Jun
£186
2 Jun - 3 Jun
includes taxes & fees
8/10 Very Good! (10,145 reviews)
"Very good location right in the heart of Downtown Chicago."

Reviewed on 26 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is £232 per night from 16 Jun to 17 Jun
£232
16 Jun - 17 Jun
includes taxes & fees
9.4/10 Exceptional! (4,263 reviews)
"The staff is very helpful, always ready to answer any question about the hotel or about the city of Chicago. The hotel is very clean , the breakfast is very good with many choices and the staff in the restaurant is excellent. My wife and I stayed in that place for eight days and seven nights and ..."

Reviewed on 27 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is £167 per night from 21 Jun to 22 Jun
£167
21 Jun - 22 Jun
includes taxes & fees
7.8/10 Good! (1,476 reviews)
"Everything"

Reviewed on 27 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,778 properties in Lower West Side
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Lower West Side travel package cost?
Handcraft your Lower West Side package from an affordable . Choose from any combination of hotels, flights and rental cars to craft the getaway you've been dreaming about for ages. Be sure to add on some activities and experiences!
If I'm not able to travel, can I cancel my Lower West Side travel package?
Yes, you can. We realise even the best-laid plans can fail, so we're here to help if you have to make changes to your Lower West Side travel package. You may be able to amend or cancel your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if your booking was made more than 24 hours ago. Head to our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.
How do I get a cheap travel package to Lower West Side?
One of the easiest ways to save dollars (and time) is to combine your bookings with Expedia. Hotels, flights, rental cars and activities — we've got them all covered. Choose the combination that best suits you and see your savings grow. We know a travel package is never a one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 hotel options worldwide, which lets you customize your Lower West Side getaway.
Does Expedia offer Book Now, Pay Later Lower West Side holidays?
We do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply click on the payment plan best suited to your needs during the checkout process and take away the stress of budgeting for your next trip. Remember to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna has convenient monthly payment plans that work for all types of budgets, so you can have that well-deserved holiday now.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your trip in multiple transactions.
  • Low deposit holidays: When you want to jump on an awesome deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock it in.

Where should I stay in Lower West Side?
Take the leg work out of sightseeing by staying in a hotel just a stone's throw away from Lower West Side's terrific attractions. Millennium Park and Wrigley Field are two of the best in this neighbourhood.
What are the top hotels in Lower West Side?
Hyatt Regency Chicago and The Godfrey Hotel Chicago are a couple of the most popular properties in Lower West Side. Why not check out the rates and amenities at each and then make up your mind?
How far in advance should I book my Lower West Side holiday?
It can be tricky to know when is the ideal time to book your Lower West Side trip. But generally the earlier you book, the more affordable the prices. Sometimes, you can book your flights and hotels nearly 12 months prior to departure. If you're eager to escape on a last-minute getaway, no need to panic! There are plenty of fantastic bargains advertised on Expedia every single day.
What does an Expedia Lower West Side travel package include?
Much of that depends on you. You can pick from a variety of Lower West Side packages, such as a rental car, flight and hotel. You can also book a hotel with a flight, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like activities and experiences. Whatever your Lower West Side trip looks like, get ready to save!
What should I know before booking a Lower West Side travel package?
Find deals that match your budget with an Expedia package. Hotels, flights, rental cars — we have everything you need to plan your break. You'll save big bucks just by bundling your bookings. Whether you're going on a ski trip or drinking cocktails on a beach, your dream getaway is only clicks away.
Can I choose my airline with a Lower West Side Expedia travel package?
You can, and with over 550 airlines to select from across the globe, you have loads of choice. Browse the available options and find out which airline suits your needs and budget.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£16
per child
98% of travellers recommend
Flyover in Chicago
See all activities in Chicago

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.