$29 Cheap flight deals from Houston (HOU) to Bolingbrook (CHI)

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This Weekend's Flight Deals from Houston to Bolingbrook

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jan 2 - Mon, Jan 5
IAH
George Bush Intercontinental
MDW
Midway Intl.
$363 Roundtrip, found 7 hours ago
$363
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Fri, Jan 2 from George Bush Intercontinental to Midway Intl., returning Mon, Jan 5, priced at $363 found 7 hours ago
Fri, Jan 2 - Mon, Jan 5
IAH
George Bush Intercontinental
MDW
Midway Intl.
$363 Roundtrip, found 7 hours ago
$363
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Fri, Jan 2 from George Bush Intercontinental to Midway Intl., returning Mon, Jan 5, priced at $363 found 7 hours ago
Sun, Jan 4 - Mon, Jan 5
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$382 Roundtrip, found 6 hours ago
$382
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sun, Jan 4 from George Bush Intercontinental to O'Hare Intl., returning Mon, Jan 5, priced at $382 found 6 hours ago
Sun, Jan 4 - Mon, Jan 5
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$382 Roundtrip, found 6 hours ago
$382
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sun, Jan 4 from George Bush Intercontinental to O'Hare Intl., returning Mon, Jan 5, priced at $382 found 6 hours ago

Airfares from $29 One Way, $68 Round Trip from Houston to Bolingbrook

Prices starting at $68 for return flights and $29 for one-way flights to Bolingbrook were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Feb 14 - Sat, Feb 21
IAH
Houston
ORD
Chicago
$68 Roundtrip, found 4 hours ago
$68
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Feb 14 from Houston to Chicago, returning Sat, Feb 21, priced at $68 found 4 hours ago
Wed, Jan 28 - Sat, Jan 31
IAH
Houston
ORD
Chicago
$72 Roundtrip, found 2 days ago
$72
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Jan 28 from Houston to Chicago, returning Sat, Jan 31, priced at $72 found 2 days ago
Mon, Feb 23 - Fri, Feb 27
IAH
Houston
MDW
Chicago
$84 Roundtrip, found 2 days ago
$84
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Houston to Chicago, returning Fri, Feb 27, priced at $84 found 2 days ago
Wed, Feb 18 - Sat, Feb 21
IAH
Houston
ORD
Chicago
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select United flight, departing Wed, Feb 18 from Houston to Chicago, returning Sat, Feb 21, priced at $157 found 1 day ago
Wed, Feb 18 - Sat, Feb 21
IAH
Houston
ORD
Chicago
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Feb 18 from Houston to Chicago, returning Sat, Feb 21, priced at $157 found 1 day ago

Bolingbrook economy flight packages

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
4.0-star property

Palmer House a Hilton Hotel

8.4/10 Very Good! (2,059 reviews)

Feb 14 - Feb 16

2 night stay

Houston (HOU) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $289, price is now $197 per person
$197
per person
found 1 day ago
No hand soap in our room, shower curtain was filthy and there were clothes from a previous giuest in the bureau. Reprehensible.

Reviewed on Dec 28, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Feb 14 - Feb 16

2 night stay

Houston (HOU) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $327, price is now $214 per person
$214
per person
found 1 day ago
Staff is TOP NOTCH! I am in a wheelchair right now, recovering from a knee surgery, and staff could not have been more solicitous and helpful. Also, when we checked in, upon learning of my daughter‘s birthday on Christmas, the front desk representative gave us a complementary room upgrade and sent up chocolates! The room was very clean and the shower was fantastic. Not enough good words about the buffet, as long as you’re clear that it is a “breakfast“ buffet and not a “brunch“ buffet :-). I think I was expecting a sliced roast beef and an omelette bar, but it is in fact a very extensive selection of breakfast foods. The restaurant recommendation was spot on. We had a delicious dinner of fine Mediterranean/Sardinian foodat Nora’s next door and enjoyed it immensely. I have now joined the capital RIU club and plan on spending much more time at their other properties, particularly in Costa Rica, where I am moving next month. Kudos to all, and thank you for our wonderful stay!

Reviewed on Dec 28, 2025

Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (2,008 reviews)

Feb 14 - Feb 16

2 night stay

Houston (HOU) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $300, price is now $211 per person
$211
per person
found 1 day ago
Solid place to stay

Reviewed on Nov 5, 2025

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More About Flying To Bolingbrook from Houston

Route Information for Flights from Houston to Bolingbrook

Origin Airport IATA Code
HOU
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Houston to Bolingbrook

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.