Prairie District Holidays

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Photo by Susie Morgan

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    Packages with flights are ATOL protected

Your Prairie District Holiday

Book your holiday package to Prairie District and prepare to experience its culture and more. Whether you're craving adventure or fun, you'll find it in this inviting neighbourhood. Not sure where to go during your trip to Prairie District? Nearby attractions like Millennium Park, Willis Tower and Art Institute of Chicago are excellent places to start. Whatever your travel goals or the size of your budget, booking a perfect Prairie District holiday has never been easier with Expedia.

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

    Hilton Garden Inn Chicago Downtown South Loop + Flight

    Downtown Chicago
    5 nights
    3.0 star property
    8.8/10 - Excellent (2,016 reviews)
    "."
    Reviewed May 28, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £3,740
    £2,294
    per traveller
    found 1 day ago
    Hilton Garden Inn Chicago Downtown South Loop
  • Studio, 2 Double Beds | Bathroom | Shower, free toiletries, hair dryer, towels
    Aug 3 - Aug 8

    Sports Illustrated Resorts Chicago + Flight

    Downtown Chicago
    5 nights
    3.5 star property
    9.2/10 - Wonderful (1,391 reviews)
    "Shea was wondering! A couple of hiccups but she handled with ease. I would definitely stay again because of the service I received."
    Reviewed May 27, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £3,801
    £2,308
    per traveller
    found 1 day ago
    Sports Illustrated Resorts Chicago
  • 2 bars/lounges, rooftop bar
    Aug 3 - Aug 8

    theWit Chicago, a Hilton Hotel + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (1,000 reviews)
    "Great location. Staff was professional and helpful. Restaurant State and Lake had great breakfast and ambience. Roof at theWit was amazing with a good happy hour, great ambience and vibe with city views."
    Reviewed May 27, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £4,011
    £2,455
    per traveller
    found 1 day ago
    theWit Chicago, a Hilton Hotel
  • Meeting facility
    Aug 3 - Aug 8

    Thompson Chicago, by Hyatt + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.2/10 - Wonderful (1,374 reviews)
    "Such a gorgeous hotel. And it’s in the Gold Coast neighbour of Chicago so you are in the middle of all the energy and excitement of the city. Absolutely amazing."
    Reviewed May 28, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £3,920
    £2,403
    per traveller
    found 1 day ago
    Thompson Chicago, by Hyatt
  • Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers
    Aug 3 - Aug 8

    Holiday Inn & Suites Chicago - Downtown by IHG + Flight

    Downtown Chicago
    5 nights
    3.0 star property
    8.6/10 - Excellent (1,009 reviews)
    "nice room"
    Reviewed May 29, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £3,905
    £2,404
    per traveller
    found 1 day ago
    Holiday Inn & Suites Chicago - Downtown by IHG

Where to stay in Prairie District

Find the best Prairie District areas and neighborhoods for the activities you enjoy most. Learn more about Prairie District
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 Prairie District

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is £115 per night from 29 Jun to 30 Jun
£115
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,124 reviews)
"Great location and clean"

Reviewed on 29 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £188 per night from 30 Jun to 1 Jul
£188
30 Jun - 1 Jul
includes taxes & fees
9.4/10 Exceptional! (4,288 reviews)
"Staff was super nice and attentive."

Reviewed on 29 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
Fully refundable
The price is £134 per night from 28 Jun to 29 Jun
£134
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,488 reviews)
"rooftop"

Reviewed on 29 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,618 properties in Prairie District
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 Prairie District travel package cost?
Cross off another part of the world with our Prairie District travel packages, which start from only . Handpick the hotels and flights that suit your style. Then, add on one or two sightseeing activities for an incredible getaway.
If I'm not able to travel, can I cancel my Prairie District travel package?
Your situation can change in a flash, so yes. You may be able to change or cancel your Prairie District travel package for free within 24 hours of booking. For bookings older than that, you can still make changes, but your car rental company, hotel or airline may charge a fee. Looking for more information? Visit our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Prairie District?
One of the easiest ways to save cash (and time) is to bundle your bookings with Expedia. Flights, rental cars, hotels and activities — we've got them all covered. Select the combination that suits your style and see your savings grow. We know a package deal is never one-size-fits-all. That's why Expedia offers over 550 airlines and 1,000,000 hotel options throughout the world, which lets you customize your Prairie District getaway.
Does Expedia offer Book Now, Pay Later Prairie District holidays?
Expedia has joined forces with online lender Klarna to make booking your next getaway a little easier on the wallet. Paying by instalment means you can spread the costs of your next dream escape, leaving you with more money to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find one that falls within your budget. Check out these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If making small repayments each month sounds right for you, pick this option at checkout.
  • Pay in instalments holidays: If you want to pay off your getaway in multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you see an awesome deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock it in.

Where should I stay in Prairie District?
Most visitors to Prairie District include both Millennium Park and Wrigley Field on their must-see lists. Why not consider a hotel near these fantastic attractions?
What are the top hotels in Prairie District?
Hyatt Regency Chicago and The Godfrey Hotel Chicago are a couple of the most well-known properties in Prairie District. Why not have a look at the amenities and rates at each and then make a decision?
How far in advance should I book my Prairie District holiday?
It all depends on the air carrier, but it's usually possible to browse through international fares on Expedia up to a year in advance. While it's a good idea to book ahead of time, lucky travellers will sometimes score a cheaper seat only weeks before departure dates.
What does an Expedia Prairie District travel package include?
With Expedia, you can select a combination of flights, car rentals and hotels to create your perfect Prairie District package. Once you've made your booking, you can add on fun stuff like day tours and activities. Remember — the more you bundle, the more cash you'll save!
What should I know before booking a Prairie District travel package?
Whether it's adventure or relaxation you're after, a Prairie District travel package lets you organise your escape your way. Plus, you'll score great discounts just for combining your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Prairie District Expedia travel package?
Yes — that's one of the best things about an Expedia travel package. You're the boss! We have more than 550 partner airlines throughout the world, so you have loads of choice when creating your Prairie District trip.

Popular places to visit

Elbridge G Keith House

Learn about the local history of Chicago with a stop at Elbridge G Keith House. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Elbridge G Keith House

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

£29
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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.